(1S,2S,4R,5R,6R,7S)-6-Benzenesulfonyl-7-benzyloxymethyl-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methyl-3,8-dioxa-tricyclo[3.2.1.0^2,4]octane

Base Information

• Chemical Name: (1S,2S,4R,5R,6R,7S)-6-Benzenesulfonyl-7-benzyloxymethyl-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methyl-3,8-dioxa-tricyclo[3.2.1.0^2,4]octane
• CAS No.: 121896-31-9
• Molecular Formula: C₂₆H₃₀O₇S
• Molecular Weight: 486.586

Synonyms:(1S,2S,4R,5R,6R,7S)-6-Benzenesulfonyl-7-benzyloxymethyl-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methyl-3,8-dioxa-tricyclo[3.2.1.0^2,4]octane

Chemical Property of (1S,2S,4R,5R,6R,7S)-6-Benzenesulfonyl-7-benzyloxymethyl-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methyl-3,8-dioxa-tricyclo[3.2.1.0^2,4]octane

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (1S,2S,4R,5R,6R,7S)-6-Benzenesulfonyl-7-benzyloxymethyl-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methyl-3,8-dioxa-tricyclo[3.2.1.0^2,4]octane

There total 10 articles about (1S,2S,4R,5R,6R,7S)-6-Benzenesulfonyl-7-benzyloxymethyl-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methyl-3,8-dioxa-tricyclo[3.2.1.0^2,4]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: 55.0%

benzyl bromide (100-39-0) + [(1R,2R,4S,5S,6S,7R)-7-Benzenesulfonyl-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methyl-3,8-dioxa-tricyclo[3.2.1.02,4]oct-6-yl]-methanol (121923-70-4) → (1S,2S,4R,5R,6R,7S)-6-Benzenesulfonyl-7-benzyloxymethyl-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methyl-3,8-dioxa-tricyclo[3.2.1.02,4]octane (121896-31-9)

Guidance literature:

With sodium hydride;

DOI:10.1016/S0040-4039(00)82264-9

Reference yield:

2-methylfuran (534-22-5) → (1S,2S,4R,5R,6R,7S)-6-Benzenesulfonyl-7-benzyloxymethyl-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methyl-3,8-dioxa-tricyclo[3.2.1.02,4]octane (121896-31-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) BuLi / 1.) THF

2: NaH / tetrahydrofuran / 36 h / 25 °C

3: 97 percent / MCPBA / CH₂Cl₂ / 3 h / Heating

4: 84 percent / DIBAL

5: TsOH / 1) MeOH

6: 55 percent / NaH

With n-butyllithium; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(00)82264-9

Reference yield:

(2E)-3-(phenylthio)acrylic acid (706-02-5,63413-91-2) → (1S,2S,4R,5R,6R,7S)-6-Benzenesulfonyl-7-benzyloxymethyl-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methyl-3,8-dioxa-tricyclo[3.2.1.02,4]octane (121896-31-9)

Guidance literature:

Multi-step reaction with 7 steps

1: peracetic acid

2: SOCl₂

3: NaH / tetrahydrofuran / 36 h / 25 °C

4: 97 percent / MCPBA / CH₂Cl₂ / 3 h / Heating

5: 84 percent / DIBAL

6: TsOH / 1) MeOH

7: 55 percent / NaH

With peracetic acid; thionyl chloride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(00)82264-9

upstream raw materials:

benzyl bromide

[(1R,2R,4S,5S,6S,7R)-7-Benzenesulfonyl-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methyl-3,8-dioxa-tricyclo[3.2.1.0^2,4]oct-6-yl]-methanol

2-methylfuran

(2E)-3-(phenylthio)acrylic acid

Downstream raw materials:

(1S,2S,4S,5R,6R,7R)-1-Benzenesulfonyl-7-benzyloxymethyl-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-3-oxa-tricyclo[2.2.1.0^2,6]heptan-5-ol

Acetic acid (1S,2S,4S,5R,6R,7R)-1-benzenesulfonyl-7-benzyloxymethyl-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-3-oxa-tricyclo[2.2.1.0^2,6]hept-5-yl ester

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