(1S,2R,5S,7R)-7-(benzyloxymethyl)-2-phenylthio-6,8-dioxabicyclo[3.2.1]oct-3-ene

Base Information

• Chemical Name: (1S,2R,5S,7R)-7-(benzyloxymethyl)-2-phenylthio-6,8-dioxabicyclo[3.2.1]oct-3-ene
• CAS No.: 1283695-39-5
• Molecular Formula: C₂₀H₂₀O₃S
• Molecular Weight: 340.443
• Mol file: 1283695-39-5.mol

Synonyms:(1S,2R,5S,7R)-7-(benzyloxymethyl)-2-phenylthio-6,8-dioxabicyclo[3.2.1]oct-3-ene

Chemical Property of (1S,2R,5S,7R)-7-(benzyloxymethyl)-2-phenylthio-6,8-dioxabicyclo[3.2.1]oct-3-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,5S,7R)-7-(benzyloxymethyl)-2-phenylthio-6,8-dioxabicyclo[3.2.1]oct-3-ene

There total 1 articles about (1S,2R,5S,7R)-7-(benzyloxymethyl)-2-phenylthio-6,8-dioxabicyclo[3.2.1]oct-3-ene 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: 86.0%

diphenyldisulfane (882-33-7) + (1R,2S,5S,7R)-7-(benzyloxymethyl)-6,8-dioxabicyclo[3.2.1]oct-3-en-2-ol (243987-96-4) → (1S,2R,5S,7R)-7-(benzyloxymethyl)-2-phenylthio-6,8-dioxabicyclo[3.2.1]oct-3-ene (1283695-39-5)

Guidance literature:

With pyridine; tributylphosphine; at 0 - 60 ℃; for 16h; Inert atmosphere;

DOI:10.1002/anie.201007327

Reference yield: 71.0%

(1S,2R,5S,7R)-7-(benzyloxymethyl)-2-phenylthio-6,8-dioxabicyclo[3.2.1]oct-3-ene (1283695-39-5) → (1R,4S,5R,7R)-7-(benzyloxymethyl)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-ol (1283695-41-9)

Guidance literature:

(1S,2R,5S,7R)-7-(benzyloxymethyl)-2-phenylthio-6,8-dioxabicyclo[3.2.1]oct-3-ene; With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 ℃; for 1.5h; Inert atmosphere;

With phosphorous acid trimethyl ester; In ethanol; dichloromethane; at -78 ℃; for 6h; Inert atmosphere; Reflux;

DOI:10.1002/anie.201007327

Reference yield:

(1S,2R,5S,7R)-7-(benzyloxymethyl)-2-phenylthio-6,8-dioxabicyclo[3.2.1]oct-3-ene (1283695-39-5) → (1R,4S,5R,7R)-7-(benzyloxymethyl)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-yloxy tert-butyldimethylsilane (1283695-54-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.5 h / -78 °C / Inert atmosphere

1.2: 6 h / -78 °C / Inert atmosphere; Reflux

2.1: 1H-imidazole; dmap; tert-butyldimethylsilyl chloride / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; dmap; tert-butyldimethylsilyl chloride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1002/anie.201007327

upstream raw materials:

diphenyldisulfane

(1R,2S,5S,7R)-7-(benzyloxymethyl)-6,8-dioxabicyclo[3.2.1]oct-3-en-2-ol

Downstream raw materials:

(1R,4S,5R,7R)-7-(benzyloxymethyl)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-ol

(1R,4S,5R,7R)-7-(benzyloxymethyl)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-yloxy tert-butyldimethylsilane