(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

Base Information

• Chemical Name: (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
• CAS No.: 121896-32-0
• Molecular Formula: C₂₆H₃₀O₇S
• Molecular Weight: 486.586

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Technology Process of (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

There total 11 articles about (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 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: 100.0%

(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) → (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[2.2.1.02,6]heptan-5-ol (121896-32-0)

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 0.25h;

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

Reference yield:

2-methylfuran (534-22-5) → (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[2.2.1.02,6]heptan-5-ol (121896-32-0)

Guidance literature:

Multi-step reaction with 7 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

7: 100 percent / KN(TMS)2 / tetrahydrofuran / 0.25 h / -78 °C

With n-butyllithium; potassium hexamethylsilazane; 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,4S,5R,6R,7R)-1-Benzenesulfonyl-7-benzyloxymethyl-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-3-oxa-tricyclo[2.2.1.02,6]heptan-5-ol (121896-32-0)

Guidance literature:

Multi-step reaction with 8 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

8: 100 percent / KN(TMS)2 / tetrahydrofuran / 0.25 h / -78 °C

With peracetic acid; thionyl chloride; potassium hexamethylsilazane; 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:

(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

2-methylfuran

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

3-phenylsulfonyl-2(Z)-propenoic acid

Downstream raw materials:

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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