(1S,3R,5R,7S)-7-Benzyl-3-(toluene-4-sulfonyl)-6,8-dioxa-bicyclo[3.2.1]octane

Base Information

• Chemical Name: (1S,3R,5R,7S)-7-Benzyl-3-(toluene-4-sulfonyl)-6,8-dioxa-bicyclo[3.2.1]octane
• CAS No.: 89927-14-0
• Molecular Formula: C₂₀H₂₂O₄S
• Molecular Weight: 358.458
• Mol file: 89927-14-0.mol

Synonyms:(1S,3R,5R,7S)-7-Benzyl-3-(toluene-4-sulfonyl)-6,8-dioxa-bicyclo[3.2.1]octane

Chemical Property of (1S,3R,5R,7S)-7-Benzyl-3-(toluene-4-sulfonyl)-6,8-dioxa-bicyclo[3.2.1]octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R,5R,7S)-7-Benzyl-3-(toluene-4-sulfonyl)-6,8-dioxa-bicyclo[3.2.1]octane

There total 4 articles about (1S,3R,5R,7S)-7-Benzyl-3-(toluene-4-sulfonyl)-6,8-dioxa-bicyclo[3.2.1]octane 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: 53.0%

Toluene-4-sulfonic acid (1S,3R,5S,7S)-3-(toluene-4-sulfonyl)-6,8-dioxa-bicyclo[3.2.1]oct-7-ylmethyl ester (88948-52-1) → (1S,3R,5R,7S)-7-Benzyl-3-(toluene-4-sulfonyl)-6,8-dioxa-bicyclo[3.2.1]octane (89927-14-0)

Guidance literature:

With lithium diphenylcuprate;

DOI:10.1016/S0040-4039(01)91157-8

Reference yield:

{(4S,5S)-5-Hydroxymethyl-2-[2-(toluene-4-sulfonyl)-ethyl]-[1,3]dioxolan-4-yl}-methanol (88948-50-9) → (1S,3R,5R,7S)-7-Benzyl-3-(toluene-4-sulfonyl)-6,8-dioxa-bicyclo[3.2.1]octane (89927-14-0)

Guidance literature:

Multi-step reaction with 3 steps

1: sulfonation

2: intramolecular alkylation

3: 53 percent / Ph₂CuLi

With lithium diphenylcuprate;

DOI:10.1016/S0040-4039(01)91157-8

Reference yield:

(4R,5R)-2-[2-(Toluene-4-sulfonyl)-ethyl]-[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester (88948-49-6) → (1S,3R,5R,7S)-7-Benzyl-3-(toluene-4-sulfonyl)-6,8-dioxa-bicyclo[3.2.1]octane (89927-14-0)

Guidance literature:

Multi-step reaction with 4 steps

1: reduction

2: sulfonation

3: intramolecular alkylation

4: 53 percent / Ph₂CuLi

With lithium diphenylcuprate;

DOI:10.1016/S0040-4039(01)91157-8

upstream raw materials:

Toluene-4-sulfonic acid (1S,3R,5S,7S)-3-(toluene-4-sulfonyl)-6,8-dioxa-bicyclo[3.2.1]oct-7-ylmethyl ester

{(4S,5S)-5-Hydroxymethyl-2-[2-(toluene-4-sulfonyl)-ethyl]-[1,3]dioxolan-4-yl}-methanol

(4R,5R)-2-[2-(Toluene-4-sulfonyl)-ethyl]-[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester

C₂₈H₃₂O₁₀S₃

Downstream raw materials:

Acetic acid (S)-2-phenyl-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-ethyl ester