(S)-5-[(3aS,4R,6R,7R,7aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid benzyl ester

Base Information

Chemical Name:(S)-5-[(3aS,4R,6R,7R,7aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid benzyl ester
CAS No.:178181-75-4
Molecular Formula:C₅₂H₅₉NO₁₀Si
Molecular Weight:886.127
Hs Code.:

(S)-5-[(3aS,4R,6R,7R,7aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid benzyl ester

Synonyms:(S)-5-[(3aS,4R,6R,7R,7aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid benzyl ester

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Chemical Property of (S)-5-[(3aS,4R,6R,7R,7aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid benzyl ester

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Technology Process of (S)-5-[(3aS,4R,6R,7R,7aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid benzyl ester

There total 5 articles about (S)-5-[(3aS,4R,6R,7R,7aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid benzyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 137792-66-6
phenyl 6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-D-galactal

: 178181-75-4
(S)-5-[(3aS,4R,6R,7R,7aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: dimethyldioxirane / acetone; CH₂Cl₂ / 1 h / 0 °C

2: ZnCl₂, molecular sieves AW-300 / tetrahydrofuran; diethyl ether / 18 h / -50 - 20 °C

With 3 A molecular sieve; 3,3-dimethyldioxirane; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; acetone;
DOI:10.1016/S0040-4020(98)83057-3

Reference yield:

: 178181-74-3
benzyl (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-hydroxypentanoate

: 214468-40-3
1,2-dihydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-α-D-galactopyranoside

: 178181-75-4
(S)-5-[(3aS,4R,6R,7R,7aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid benzyl ester

Guidance literature:: With molecular sieve; zinc(II) chloride; Yield given. Multistep reaction; 1.) THF, RT, 30 min, 2.) THF, Et₂O, RT, 19 h;
DOI:10.1021/ja980489k

Reference yield:

: 122350-52-1
(4S)-5-benzyloxy-4-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxopentanoic acid

: 178181-75-4
(S)-5-[(3aS,4R,6R,7R,7aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 4-methylmorpholine / tetrahydrofuran / 0.5 h / -10 °C

2: NaBH₄ / methanol / 0.5 h / 0 °C

3: ZnCl₂, molecular sieves AW-300 / tetrahydrofuran; diethyl ether / 18 h / -50 - 20 °C

With 4-methyl-morpholine; sodium tetrahydroborate; 3 A molecular sieve; zinc(II) chloride; In tetrahydrofuran; methanol; diethyl ether;
DOI:10.1016/S0040-4020(98)83057-3