(4aR,6R,7R,8S,8aR)-3-((S)-2-Amino-2-benzyloxycarbonyl-ethyl)-7,8-bis-benzyloxy-6-benzyloxymethyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (4aR,6R,7R,8S,8aR)-3-((S)-2-Amino-2-benzyloxycarbonyl-ethyl)-7,8-bis-benzyloxy-6-benzyloxymethyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid methyl ester
• CAS No.: 766514-54-9
• Molecular Formula: C₄₁H₄₃NO₉S
• Molecular Weight: 725.86

Synonyms:(4aR,6R,7R,8S,8aR)-3-((S)-2-Amino-2-benzyloxycarbonyl-ethyl)-7,8-bis-benzyloxy-6-benzyloxymethyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid methyl ester

Chemical Property of (4aR,6R,7R,8S,8aR)-3-((S)-2-Amino-2-benzyloxycarbonyl-ethyl)-7,8-bis-benzyloxy-6-benzyloxymethyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid methyl ester

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Technology Process of (4aR,6R,7R,8S,8aR)-3-((S)-2-Amino-2-benzyloxycarbonyl-ethyl)-7,8-bis-benzyloxy-6-benzyloxymethyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid methyl ester

There total 3 articles about (4aR,6R,7R,8S,8aR)-3-((S)-2-Amino-2-benzyloxycarbonyl-ethyl)-7,8-bis-benzyloxy-6-benzyloxymethyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid methyl 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:

1-O-2-S-[1'-benzyloxycarbonyl-2'-(4'-t-butoxycarbonylamino)-methylpropionate-1'-2'-ethenyl]-3,4,6-tri-O-benzyl-α-D-glucopyranoside (766514-49-2) → (4aR,6R,7R,8S,8aR)-3-((S)-2-Amino-2-benzyloxycarbonyl-ethyl)-7,8-bis-benzyloxy-6-benzyloxymethyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid methyl ester (766514-54-9)

Guidance literature:

With chloro-trimethyl-silane; phenol; In dichloromethane;

DOI:10.1021/jo049441h

Reference yield:

2-[[(1,1-dimethylethoxy)carbonyl]amino]-4-oxo-hexanedioic acid 6-methyl 1-(phenylmethyl) ester (630128-01-7) → (4aR,6R,7R,8S,8aR)-3-((S)-2-Amino-2-benzyloxycarbonyl-ethyl)-7,8-bis-benzyloxy-6-benzyloxymethyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid methyl ester (766514-54-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / pyridine; phthalimidesulfenyl chloride / CHCl₃ / 20 h / 40 °C

2: TMSCl; phenol / CH₂Cl₂

With pyridine; chloro-trimethyl-silane; phthalimidesulfenyl chloride; phenol; In dichloromethane; chloroform;

DOI:10.1021/jo049441h

Reference yield:

2-tert-butoxycarbonylamino-4-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidene)-4-hydroxy-butyric acid benzyl ester (844644-72-0) → (4aR,6R,7R,8S,8aR)-3-((S)-2-Amino-2-benzyloxycarbonyl-ethyl)-7,8-bis-benzyloxy-6-benzyloxymethyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid methyl ester (766514-54-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / benzene / 5 h / Heating

2: 68 percent / pyridine; phthalimidesulfenyl chloride / CHCl₃ / 20 h / 40 °C

3: TMSCl; phenol / CH₂Cl₂

With pyridine; chloro-trimethyl-silane; phthalimidesulfenyl chloride; phenol; In dichloromethane; chloroform; benzene;

DOI:10.1021/jo049441h

upstream raw materials:

1-O-2-S-[1'-benzyloxycarbonyl-2'-(4'-t-butoxycarbonylamino)-methylpropionate-1'-2'-ethenyl]-3,4,6-tri-O-benzyl-α-D-glucopyranoside

2-[[(1,1-dimethylethoxy)carbonyl]amino]-4-oxo-hexanedioic acid 6-methyl 1-(phenylmethyl) ester

2-tert-butoxycarbonylamino-4-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidene)-4-hydroxy-butyric acid benzyl ester

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