(4aR,6R,7S,8S,8aR)-3-[(S)-2-Benzyloxycarbonyl-2-(2-naphthalen-2-yl-acetylamino)-ethyl]-7,8-dihydroxy-6-hydroxymethyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid

Base Information

• Chemical Name: (4aR,6R,7S,8S,8aR)-3-[(S)-2-Benzyloxycarbonyl-2-(2-naphthalen-2-yl-acetylamino)-ethyl]-7,8-dihydroxy-6-hydroxymethyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid
• CAS No.: 766514-68-5
• Molecular Formula: C₃₁H₃₁NO₁₀S
• Molecular Weight: 609.654
• Mol file: 766514-68-5.mol

Synonyms:(4aR,6R,7S,8S,8aR)-3-[(S)-2-Benzyloxycarbonyl-2-(2-naphthalen-2-yl-acetylamino)-ethyl]-7,8-dihydroxy-6-hydroxymethyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid

Chemical Property of (4aR,6R,7S,8S,8aR)-3-[(S)-2-Benzyloxycarbonyl-2-(2-naphthalen-2-yl-acetylamino)-ethyl]-7,8-dihydroxy-6-hydroxymethyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,6R,7S,8S,8aR)-3-[(S)-2-Benzyloxycarbonyl-2-(2-naphthalen-2-yl-acetylamino)-ethyl]-7,8-dihydroxy-6-hydroxymethyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid

There total 5 articles about (4aR,6R,7S,8S,8aR)-3-[(S)-2-Benzyloxycarbonyl-2-(2-naphthalen-2-yl-acetylamino)-ethyl]-7,8-dihydroxy-6-hydroxymethyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid 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: 65.0%

(4aR,6R,7R,8S,8aR)-3-[(S)-2-Benzyloxycarbonyl-2-(2-naphthalen-2-yl-acetylamino)-ethyl]-7-hydroxy-6-hydroxymethyl-8-triisopropylsilanyloxy-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester (766514-66-3) → (4aR,6R,7S,8S,8aR)-3-[(S)-2-Benzyloxycarbonyl-2-(2-naphthalen-2-yl-acetylamino)-ethyl]-7,8-dihydroxy-6-hydroxymethyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid (766514-68-5)

Guidance literature:

With cesium fluoride; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1021/jo049441h

Reference yield:

2-tert-butoxycarbonylamino-4-oxo-hexanedioic acid 1-benzyl ester 6-(2-trimethylsilanyl-ethyl) ester (766514-48-1) → (4aR,6R,7S,8S,8aR)-3-[(S)-2-Benzyloxycarbonyl-2-(2-naphthalen-2-yl-acetylamino)-ethyl]-7,8-dihydroxy-6-hydroxymethyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid (766514-68-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 40 percent / pyridine; phthalimidesulfenyl chloride / CHCl₃ / 40 h / 50 - 55 °C

2: TMSCl / CH₂Cl₂ / 1.5 h / 20 °C

3: 43 percent / NEt₃ / CH₂Cl₂ / 2 h / 20 °C

4: 65 percent / CsF / dimethylformamide / 24 h / 20 °C

With pyridine; chloro-trimethyl-silane; phthalimidesulfenyl chloride; triethylamine; cesium fluoride; In dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/jo049441h

Reference yield:

(4aR,6R,7R,8S,8aR)-3-((S)-2-Benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-7-hydroxy-8-triisopropylsilanyloxy-6-triisopropylsilanyloxymethyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester (766514-63-0) → (4aR,6R,7S,8S,8aR)-3-[(S)-2-Benzyloxycarbonyl-2-(2-naphthalen-2-yl-acetylamino)-ethyl]-7,8-dihydroxy-6-hydroxymethyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid (766514-68-5)

Guidance literature:

Multi-step reaction with 3 steps

1: TMSCl / CH₂Cl₂ / 1.5 h / 20 °C

2: 43 percent / NEt₃ / CH₂Cl₂ / 2 h / 20 °C

3: 65 percent / CsF / dimethylformamide / 24 h / 20 °C

With chloro-trimethyl-silane; triethylamine; cesium fluoride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo049441h

upstream raw materials:

(4aR,6R,7R,8S,8aR)-3-[(S)-2-Benzyloxycarbonyl-2-(2-naphthalen-2-yl-acetylamino)-ethyl]-7-hydroxy-6-hydroxymethyl-8-triisopropylsilanyloxy-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester

2-tert-butoxycarbonylamino-4-oxo-hexanedioic acid 1-benzyl ester 6-(2-trimethylsilanyl-ethyl) ester

(4aR,6R,7R,8S,8aR)-3-((S)-2-Amino-2-benzyloxycarbonyl-ethyl)-7-hydroxy-6-hydroxymethyl-8-triisopropylsilanyloxy-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester

(4aR,6R,7R,8S,8aR)-3-((S)-2-Benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-7-hydroxy-8-triisopropylsilanyloxy-6-triisopropylsilanyloxymethyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester