Acetic acid (3aR,4S,6S,7R,7aS)-4-acetoxymethyl-2-oxo-6-phenylsulfanyl-3-((1R,4R,5S,6S)-4,5,6-triacetoxy-3-acetoxymethyl-cyclohex-2-enyl)-hexahydro-pyrano[3,4-d]oxazol-7-yl ester

Base Information

• Chemical Name: Acetic acid (3aR,4S,6S,7R,7aS)-4-acetoxymethyl-2-oxo-6-phenylsulfanyl-3-((1R,4R,5S,6S)-4,5,6-triacetoxy-3-acetoxymethyl-cyclohex-2-enyl)-hexahydro-pyrano[3,4-d]oxazol-7-yl ester
• CAS No.: 176389-20-1
• Molecular Formula: C₃₂H₃₇NO₁₅S
• Molecular Weight: 707.709
• Mol file: 176389-20-1.mol

Synonyms:Acetic acid (3aR,4S,6S,7R,7aS)-4-acetoxymethyl-2-oxo-6-phenylsulfanyl-3-((1R,4R,5S,6S)-4,5,6-triacetoxy-3-acetoxymethyl-cyclohex-2-enyl)-hexahydro-pyrano[3,4-d]oxazol-7-yl ester

Chemical Property of Acetic acid (3aR,4S,6S,7R,7aS)-4-acetoxymethyl-2-oxo-6-phenylsulfanyl-3-((1R,4R,5S,6S)-4,5,6-triacetoxy-3-acetoxymethyl-cyclohex-2-enyl)-hexahydro-pyrano[3,4-d]oxazol-7-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (3aR,4S,6S,7R,7aS)-4-acetoxymethyl-2-oxo-6-phenylsulfanyl-3-((1R,4R,5S,6S)-4,5,6-triacetoxy-3-acetoxymethyl-cyclohex-2-enyl)-hexahydro-pyrano[3,4-d]oxazol-7-yl ester

There total 4 articles about Acetic acid (3aR,4S,6S,7R,7aS)-4-acetoxymethyl-2-oxo-6-phenylsulfanyl-3-((1R,4R,5S,6S)-4,5,6-triacetoxy-3-acetoxymethyl-cyclohex-2-enyl)-hexahydro-pyrano[3,4-d]oxazol-7-yl 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: 82.0%

thiophenol (108-98-5) + Acetic acid (1S,2R,5R,6S)-5,6-diacetoxy-2-((3aR,4S,6R,7R,7aS)-7-acetoxy-4-acetoxymethyl-6-bromo-2-oxo-tetrahydro-pyrano[3,4-d]oxazol-3-yl)-4-acetoxymethyl-cyclohex-3-enyl ester (176389-19-8) → Acetic acid (3aR,4S,6S,7R,7aS)-4-acetoxymethyl-2-oxo-6-phenylsulfanyl-3-((1R,4R,5S,6S)-4,5,6-triacetoxy-3-acetoxymethyl-cyclohex-2-enyl)-hexahydro-pyrano[3,4-d]oxazol-7-yl ester (176389-20-1)

Guidance literature:

With triethylamine; In dichloromethane; at 5 ℃; for 2h;

DOI:10.1071/C96156

Reference yield: 54.0%

phenylthiotrimethylsilane (4551-15-9) + Acetic acid (3aR,4S,7R,7aS)-6-acetoxy-4-acetoxymethyl-2-oxo-3-((1R,4R,5S,6S)-4,5,6-triacetoxy-3-acetoxymethyl-cyclohex-2-enyl)-hexahydro-pyrano[3,4-d]oxazol-7-yl ester (190446-28-7) → Acetic acid (3aR,4S,6S,7R,7aS)-4-acetoxymethyl-2-oxo-6-phenylsulfanyl-3-((1R,4R,5S,6S)-4,5,6-triacetoxy-3-acetoxymethyl-cyclohex-2-enyl)-hexahydro-pyrano[3,4-d]oxazol-7-yl ester (176389-20-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 60 ℃; for 12h;

DOI:10.1071/C96156

Reference yield:

Acetic acid (3aR,4S,7R,7aS)-6-acetoxy-4-acetoxymethyl-2-oxo-3-((1R,4R,5S,6S)-4,5,6-triacetoxy-3-acetoxymethyl-cyclohex-2-enyl)-hexahydro-pyrano[3,4-d]oxazol-7-yl ester (190446-28-7) → Acetic acid (3aR,4S,6S,7R,7aS)-4-acetoxymethyl-2-oxo-6-phenylsulfanyl-3-((1R,4R,5S,6S)-4,5,6-triacetoxy-3-acetoxymethyl-cyclohex-2-enyl)-hexahydro-pyrano[3,4-d]oxazol-7-yl ester (176389-20-1)

Guidance literature:

Multi-step reaction with 2 steps

1: HBr / acetic acid

2: Et₃N / CH₂Cl₂

With hydrogen bromide; triethylamine; In dichloromethane; acetic acid;

DOI:10.1016/0040-4039(96)00298-5

upstream raw materials:

thiophenol

Acetic acid (1S,2R,5R,6S)-5,6-diacetoxy-2-((3aR,4S,6R,7R,7aS)-7-acetoxy-4-acetoxymethyl-6-bromo-2-oxo-tetrahydro-pyrano[3,4-d]oxazol-3-yl)-4-acetoxymethyl-cyclohex-3-enyl ester

phenylthiotrimethylsilane

Acetic acid (3aR,4S,7R,7aS)-6-acetoxy-4-acetoxymethyl-2-oxo-3-((1R,4R,5S,6S)-4,5,6-triacetoxy-3-acetoxymethyl-cyclohex-2-enyl)-hexahydro-pyrano[3,4-d]oxazol-7-yl ester

Downstream raw materials:

benzyl O-<2,3-di-O-acetyl-3,4-O,N-carbonyl-4-deoxy-4-<(1R,4R,5S,6S)-4,5,6-triacetoxy-3-(acetoxymethyl)-cyclohex-2-enyl>amino-β-D-glucopyranosyl>-(1->4)-O-(tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-tri-O-benzyl-β-D-glucopyranoside