(1R,4S,6R,7R)-benzoic acid 7-benzoyloxy-6-(tert-butyldiphenylsilanyloxy)-2-oxabicyclo[2.2.1]hept-4-ylmethyl ester

Base Information

Chemical Name:(1R,4S,6R,7R)-benzoic acid 7-benzoyloxy-6-(tert-butyldiphenylsilanyloxy)-2-oxabicyclo[2.2.1]hept-4-ylmethyl ester
CAS No.:544444-33-9
Molecular Formula:C₃₇H₃₈O₆Si
Molecular Weight:606.791
Hs Code.:

Synonyms:(1R,4S,6R,7R)-benzoic acid 7-benzoyloxy-6-(tert-butyldiphenylsilanyloxy)-2-oxabicyclo[2.2.1]hept-4-ylmethyl ester

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Chemical Property of (1R,4S,6R,7R)-benzoic acid 7-benzoyloxy-6-(tert-butyldiphenylsilanyloxy)-2-oxabicyclo[2.2.1]hept-4-ylmethyl ester

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Technology Process of (1R,4S,6R,7R)-benzoic acid 7-benzoyloxy-6-(tert-butyldiphenylsilanyloxy)-2-oxabicyclo[2.2.1]hept-4-ylmethyl ester

There total 7 articles about (1R,4S,6R,7R)-benzoic acid 7-benzoyloxy-6-(tert-butyldiphenylsilanyloxy)-2-oxabicyclo[2.2.1]hept-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: 30.0%

: 98-88-4
benzoyl chloride

: (1R,2R,4R,5R)-acetic acid 2,3-diacetoxy-1-methanesulfonyloxymethyl-4-(tert-butyldiphenylsilanyloxy)cyclopentylmethyl ester

: (1S,3R,4R,5R)-benzoic acid 4-benzoyloxy-3-(tert-butyldiphenylsilanyloxy)-6-oxabicyclo[3.2.0]hept-1-ylmethyl ester

: 544444-33-9
(1R,4S,6R,7R)-benzoic acid 7-benzoyloxy-6-(tert-butyldiphenylsilanyloxy)-2-oxabicyclo[2.2.1]hept-4-ylmethyl ester

Guidance literature:: (1R,2R,4R,5R)-acetic acid 2,3-diacetoxy-1-methanesulfonyloxymethyl-4-(tert-butyldiphenylsilanyloxy)cyclopentylmethyl ester; With potassium carbonate; In methanol; at 5 - 20 ℃;

benzoyl chloride; With triethylamine; In dichloromethane; at 0 ℃;
DOI:10.1021/ol034326z

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 544444-33-9
(1R,4S,6R,7R)-benzoic acid 7-benzoyloxy-6-(tert-butyldiphenylsilanyloxy)-2-oxabicyclo[2.2.1]hept-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 76 percent / DMAP; Et₃N / CH₂Cl₂ / 20 °C

2.1: 94 percent / OsO₄; N-methylmorpholine N-oxide monohydrate / acetone; H₂O / 20 °C

3.1: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 5 °C

4.1: 87 percent / formic acid / palladium black / methanol / 4 h / 75 °C

5.1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

6.1: K₂CO₃ / methanol / 5 - 20 °C

6.2: 53 percent / Et₃N / CH₂Cl₂ / 0 °C

With dmap; osmium(VIII) oxide; formic acid; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; palladium; In methanol; dichloromethane; water; acetone;
DOI:10.1021/ol034326z

Reference yield:

: 544444-28-2
(1R,4R)-4-Benzyloxymethyl-4-hydroxymethylcyclopent-2-en-1-ol

: 544444-33-9
(1R,4S,6R,7R)-benzoic acid 7-benzoyloxy-6-(tert-butyldiphenylsilanyloxy)-2-oxabicyclo[2.2.1]hept-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 76 percent / DMAP; Et₃N / CH₂Cl₂ / 20 °C

2.1: 94 percent / OsO₄; N-methylmorpholine N-oxide monohydrate / acetone; H₂O / 20 °C

3.1: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 5 °C

4.1: 87 percent / formic acid / palladium black / methanol / 4 h / 75 °C

5.1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

6.1: K₂CO₃ / methanol / 5 - 20 °C

6.2: 53 percent / Et₃N / CH₂Cl₂ / 0 °C

With dmap; osmium(VIII) oxide; formic acid; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; palladium; In methanol; dichloromethane; water; acetone;
DOI:10.1021/ol034326z