Helvetica chimica acta

Non??destructive Cleavage of N??Acylsultams Under Neutral Conditions: Preparation of Enantiomerically, Pure Fmoc??Protected α??Amino Acids

W Oppolzer, P Lienard

Index: Helvetica Chimica Acta, , vol. 75, # 8 p. 2572 - 2582

Full Text: HTML

Citation Number: 50

Abstract

... 2576 HELVETICA CHIMICA ACTA - Vol. 75 (1992) Table 2. Preparation of N-( (Fluoren-9-yl) methoxycarbonyl]amino Acids from N-Acylsultams by Ti( OEt),-Media- ted Propenolysis (130°//[RhCI(PPh,) ,]-Catalyzed Hydrolysis: 9 + 12 + 1 + 13 + 14 Entry - 7 8 9 I0 I1 12 ...

 Related Synthetic Route
9-Fluorenylmethyl chloroformate Structure

28920-43-6

9-Fluorenylmeth...

~%

FMOC-L-Phenylalanine Structure

35661-40-6

FMOC-L-Phenylalanine

(S)-2-amino-1-((3aS,6R,7aR)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)-3-phenylpropan-1-one Structure

168958-30-3

(S)-2-amino-1-(...

~%

FMOC-L-Phenylalanine Structure

35661-40-6

FMOC-L-Phenylalanine

(2R)-N-[(2S)-2-[[bis(methylthio)methylidene]amino]-3-phenylpropan-1-oyl]bornane-10,2-sultam Structure

127556-05-2

(2R)-N-[(2S)-2-...

~%

FMOC-L-Phenylalanine Structure

35661-40-6

FMOC-L-Phenylalanine

9-Fluorenylmethyl chloroformate Structure

28920-43-6

9-Fluorenylmeth...

~%

Fmoc-Ala-OH Structure

35661-39-3

Fmoc-Ala-OH

9-Fluorenylmethyl chloroformate Structure

28920-43-6

9-Fluorenylmeth...

~%

(S)-N-Fmoc-Allylglycine Structure

146549-21-5

(S)-N-Fmoc-Ally...

(2S)-N-(2-aminopent-4-enoyl)-(1S,2R)-bornane-10,2-sultam Structure

740769-74-8

(2S)-N-(2-amino...

~%

(S)-N-Fmoc-Allylglycine Structure

146549-21-5

(S)-N-Fmoc-Ally...

N/A Structure

127556-06-3

N/A

~%

(S)-N-Fmoc-Allylglycine Structure

146549-21-5

(S)-N-Fmoc-Ally...

9-Fluorenylmethyl chloroformate Structure

28920-43-6

9-Fluorenylmeth...

~%

Fmoc-Leu-OH Structure

35661-60-0

Fmoc-Leu-OH

(S)-2-amino-1-((3aS,6R,7aR)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)-4-methylpentan-1-one Structure

168958-29-0

(S)-2-amino-1-(...

~%

Fmoc-Leu-OH Structure

35661-60-0

Fmoc-Leu-OH

(2R)-N-((2S)-2-((bis(methylthio)methylidene)amino)-4-methylpentan-1-oyl)bornane-10,2-sultam Structure

127556-09-6

(2R)-N-((2S)-2-...

~%

Fmoc-Leu-OH Structure

35661-60-0

Fmoc-Leu-OH

N-((2R,3S)-3-hydroxy-2,4-dimethylpentanoyl)bornane-10,2-sultam Structure

125665-01-2

N-((2R,3S)-3-hy...

Allyl alcohol Structure

107-18-6

Allyl alcohol

~96%

prop-2-enyl (2R,3S)-3-hydroxy-2,4-dimethylpentanoate Structure

146549-13-5

prop-2-enyl (2R...

(2R)-Bornane-10,2-sultam Structure

94594-90-8

(2R)-Bornane-10...

2,6-PYRIDINEDICARBOXYLICACID Structure

127556-03-0

2,6-PYRIDINEDIC...

~%

(2R)-Bornane-10,2-sultam Structure

94594-90-8

(2R)-Bornane-10...

N/A Structure

168958-31-4

N/A

~%

(2R)-Bornane-10,2-sultam Structure

94594-90-8

(2R)-Bornane-10...

(S)-2-amino-1-((3aS,6R,7aR)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)-4-methylpentan-1-one Structure

168958-29-0

(S)-2-amino-1-(...

~%

(2R)-Bornane-10,2-sultam Structure

94594-90-8

(2R)-Bornane-10...

(2S)-N-(2-aminopent-4-enoyl)-(1S,2R)-bornane-10,2-sultam Structure

740769-74-8

(2S)-N-(2-amino...

~%

(2R)-Bornane-10,2-sultam Structure

94594-90-8

(2R)-Bornane-10...

(S)-2-amino-1-((3aS,6R,7aR)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)-3-phenylpropan-1-one Structure

168958-30-3

(S)-2-amino-1-(...

~%

(2R)-Bornane-10,2-sultam Structure

94594-90-8

(2R)-Bornane-10...

(2R)-N-[(2S)-2-[[bis(methylthio)methylidene]amino]propan-1-oyl]bornane-10,2-sultam Structure

127556-04-1

(2R)-N-[(2S)-2-...

~%

(2R)-Bornane-10,2-sultam Structure

94594-90-8

(2R)-Bornane-10...

N/A Structure

127556-06-3

N/A

~%

(2R)-Bornane-10,2-sultam Structure

94594-90-8

(2R)-Bornane-10...

(2R)-N-((2S)-2-((bis(methylthio)methylidene)amino)-4-methylpentan-1-oyl)bornane-10,2-sultam Structure

127556-09-6

(2R)-N-((2S)-2-...

~%

(2R)-Bornane-10,2-sultam Structure

94594-90-8

(2R)-Bornane-10...

(2R)-N-[(2S)-2-[[bis(methylthio)methylidene]amino]-3-phenylpropan-1-oyl]bornane-10,2-sultam Structure

127556-05-2

(2R)-N-[(2S)-2-...

~%

(2R)-Bornane-10,2-sultam Structure

94594-90-8

(2R)-Bornane-10...

(S)-2-amino-1-((3aS,6R,7aR)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)pent-4-yn-1-one Structure

212139-50-9

(S)-2-amino-1-(...

~%

(2R)-Bornane-10,2-sultam Structure

94594-90-8

(2R)-Bornane-10...

N-[2'-[N'-[bis(methylthio)methylidene]ammino]pent-4-ynoyl]bornane-10,2-sultam Structure

146549-05-5

N-[2'-[N'-[bis(...

~%

(2R)-Bornane-10,2-sultam Structure

94594-90-8

(2R)-Bornane-10...


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