(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

Base Information

• Chemical Name: (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
• CAS No.: 766514-63-0
• Molecular Formula: C₄₇H₈₃NO₁₁SSi₃
• Molecular Weight: 954.499
• Mol file: 766514-63-0.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 3 articles about (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 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: 40.0%

2-tert-butoxycarbonylamino-4-oxo-hexanedioic acid 1-benzyl ester 6-(2-trimethylsilanyl-ethyl) ester (766514-48-1) + 1,2-dideoxy-3,6-di-O-triisopropylsilyl-2-deoxy-D-arabino-1-hexenopyranose (343338-29-4) → (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)

Guidance literature:

With pyridine; phthalimidesulfenyl chloride; In chloroform; at 50 - 55 ℃; for 40h;

DOI:10.1021/jo049441h

Reference yield:

2-(Trimethylsilyl)ethanol (2916-68-9) → (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)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / benzene / Heating

2: 40 percent / pyridine; phthalimidesulfenyl chloride / CHCl₃ / 40 h / 50 - 55 °C

With pyridine; phthalimidesulfenyl chloride; In chloroform; benzene;

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-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)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / benzene / Heating

2: 40 percent / pyridine; phthalimidesulfenyl chloride / CHCl₃ / 40 h / 50 - 55 °C

With pyridine; phthalimidesulfenyl chloride; In chloroform; benzene;

DOI:10.1021/jo049441h

upstream raw materials:

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

1,2-dideoxy-3,6-di-O-triisopropylsilyl-2-deoxy-D-arabino-1-hexenopyranose

2-(Trimethylsilyl)ethanol

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

Downstream raw materials:

(4aR,6R,7R,8S,8aR)-3-[(S)-2-Benzyloxycarbonyl-2-(2-biphenyl-4-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

(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

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

(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