(1S,2R,3S,4R,5R,6R)-2,3,4-Tris-(4-methoxy-benzyloxy)-5-(4-methoxy-benzyloxymethyl)-7-thia-bicyclo[4.1.0]heptane

Base Information

• Chemical Name: (1S,2R,3S,4R,5R,6R)-2,3,4-Tris-(4-methoxy-benzyloxy)-5-(4-methoxy-benzyloxymethyl)-7-thia-bicyclo[4.1.0]heptane
• CAS No.: 154287-16-8
• Molecular Formula: C₃₉H₄₄O₈S
• Molecular Weight: 672.84

Synonyms:(1S,2R,3S,4R,5R,6R)-2,3,4-Tris-(4-methoxy-benzyloxy)-5-(4-methoxy-benzyloxymethyl)-7-thia-bicyclo[4.1.0]heptane

Chemical Property of (1S,2R,3S,4R,5R,6R)-2,3,4-Tris-(4-methoxy-benzyloxy)-5-(4-methoxy-benzyloxymethyl)-7-thia-bicyclo[4.1.0]heptane

Chemical Property:

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Technology Process of (1S,2R,3S,4R,5R,6R)-2,3,4-Tris-(4-methoxy-benzyloxy)-5-(4-methoxy-benzyloxymethyl)-7-thia-bicyclo[4.1.0]heptane

There total 3 articles about (1S,2R,3S,4R,5R,6R)-2,3,4-Tris-(4-methoxy-benzyloxy)-5-(4-methoxy-benzyloxymethyl)-7-thia-bicyclo[4.1.0]heptane 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: 52.0%

(1S,2R,3S,4R,5R,6S)-2,3,4-Tris-(4-methoxy-benzyloxy)-5-(4-methoxy-benzyloxymethyl)-7-oxa-bicyclo[4.1.0]heptane → (1S,2R,3S,4R,5R,6R)-2,3,4-Tris-(4-methoxy-benzyloxy)-5-(4-methoxy-benzyloxymethyl)-7-thia-bicyclo[4.1.0]heptane (154287-16-8)

Guidance literature:

With triphenylphosphine sulfide; trifluoroacetic acid; In benzene; at 60 ℃; for 48h;

DOI:10.7164/antibiotics.46.1919

Reference yield:

(1R,2R,3S,4R,5R,6S)-5-hydroxymethyl-7-oxabicyclo<4.1.0>heptane-2,3,4-triol (134680-56-1) → (1S,2R,3S,4R,5R,6R)-2,3,4-Tris-(4-methoxy-benzyloxy)-5-(4-methoxy-benzyloxymethyl)-7-thia-bicyclo[4.1.0]heptane (154287-16-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / NaH / dimethylformamide / 20 h / 25 °C

2: 52 percent / Ph₃P=S, trifluoroacetic acid / benzene / 48 h / 60 °C

With sodium hydride; triphenylphosphine sulfide; trifluoroacetic acid; In N,N-dimethyl-formamide; benzene;

DOI:10.7164/antibiotics.46.1919

Reference yield:

p-methoxybenzyl chloride (824-94-2) → (1S,2R,3S,4R,5R,6R)-2,3,4-Tris-(4-methoxy-benzyloxy)-5-(4-methoxy-benzyloxymethyl)-7-thia-bicyclo[4.1.0]heptane (154287-16-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / NaH / dimethylformamide / 20 h / 25 °C

2: 52 percent / Ph₃P=S, trifluoroacetic acid / benzene / 48 h / 60 °C

With sodium hydride; triphenylphosphine sulfide; trifluoroacetic acid; In N,N-dimethyl-formamide; benzene;

DOI:10.7164/antibiotics.46.1919

upstream raw materials:

(1R,2R,3S,4R,5R,6S)-5-hydroxymethyl-7-oxabicyclo<4.1.0>heptane-2,3,4-triol

p-methoxybenzyl chloride

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