Benzoic acid (1S,2R,4R,5R,6S,7R)-5,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,8-dioxa-tricyclo[5.1.0.0^2,4]oct-4-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (1S,2R,4R,5R,6S,7R)-5,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,8-dioxa-tricyclo[5.1.0.0^2,4]oct-4-ylmethyl ester
• CAS No.: 439213-21-5
• Molecular Formula: C₂₆H₄₂O₆Si₂
• Molecular Weight: 506.787

Synonyms:Benzoic acid (1S,2R,4R,5R,6S,7R)-5,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,8-dioxa-tricyclo[5.1.0.0^2,4]oct-4-ylmethyl ester

Chemical Property of Benzoic acid (1S,2R,4R,5R,6S,7R)-5,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,8-dioxa-tricyclo[5.1.0.0^2,4]oct-4-ylmethyl ester

Chemical Property:

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Technology Process of Benzoic acid (1S,2R,4R,5R,6S,7R)-5,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,8-dioxa-tricyclo[5.1.0.0^2,4]oct-4-ylmethyl ester

There total 6 articles about Benzoic acid (1S,2R,4R,5R,6S,7R)-5,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,8-dioxa-tricyclo[5.1.0.0^2,4]oct-4-ylmethyl ester 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: 73.0%

benzoyl chloride (98-88-4) + [(1S,2R,4R,5R,6S,7R)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-3,8-dioxa-tricyclo[5.1.0.02,4]oct-4-yl]-methanol (439213-19-1) → Benzoic acid (1S,2R,4R,5R,6S,7R)-5,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,8-dioxa-tricyclo[5.1.0.02,4]oct-4-ylmethyl ester (439213-21-5)

Guidance literature:

With pyridine; at -5 ℃; for 6h;

DOI:10.1039/b110420a

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → Benzoic acid (1S,2R,4R,5R,6S,7R)-5,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,8-dioxa-tricyclo[5.1.0.02,4]oct-4-ylmethyl ester (439213-21-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / NEt₃ / CH₂Cl₂ / 2 h / 20 °C

2: 88 percent / DIBAL-H / hexane / 3 h / 0 °C

3: 91 percent / meta-chloroperoxybenzoic acid; NaHCO₃ / CH₂Cl₂ / 3 h / 20 °C

4: 82 percent / meta-chloroperoxybenzoic acid; NaHCO₃ / CH₂Cl₂ / 16 h / 50 °C

5: 73 percent / pyridine / 6 h / -5 °C

With pyridine; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In hexane; dichloromethane;

DOI:10.1039/b110420a

Reference yield:

(2S,3S)-(+)-trans-2,3-dihydroxy-2,3-dihydrobenzoic acid (176487-06-2) → Benzoic acid (1S,2R,4R,5R,6S,7R)-5,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,8-dioxa-tricyclo[5.1.0.02,4]oct-4-ylmethyl ester (439213-21-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 81 percent / hexane; methanol / 6 h / 20 °C

2: 95 percent / NEt₃ / CH₂Cl₂ / 2 h / 20 °C

3: 88 percent / DIBAL-H / hexane / 3 h / 0 °C

4: 91 percent / meta-chloroperoxybenzoic acid; NaHCO₃ / CH₂Cl₂ / 3 h / 20 °C

5: 82 percent / meta-chloroperoxybenzoic acid; NaHCO₃ / CH₂Cl₂ / 16 h / 50 °C

6: 73 percent / pyridine / 6 h / -5 °C

With pyridine; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In methanol; hexane; dichloromethane;

DOI:10.1039/b110420a

upstream raw materials:

benzoyl chloride

[(1S,2R,4R,5R,6S,7R)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-3,8-dioxa-tricyclo[5.1.0.0^2,4]oct-4-yl]-methanol

t-butyldimethylsiyl triflate

(2S,3S)-(+)-trans-2,3-dihydroxy-2,3-dihydrobenzoic acid

Downstream raw materials:

benzoic acid 5,6-dihydroxy-3,8-dioxatricyclo[5.1.0.0^2,4]oct-4-ylmethyl ester

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