Acetic acid (3aS,5R,6S,7R,7aR)-6-benzyloxy-5-(tert-butyl-dimethyl-silanyloxymethyl)-hexahydro-1,3,4-trioxa-cyclopropa[a]naphthalen-7-yl ester

Base Information

Chemical Name:Acetic acid (3aS,5R,6S,7R,7aR)-6-benzyloxy-5-(tert-butyl-dimethyl-silanyloxymethyl)-hexahydro-1,3,4-trioxa-cyclopropa[a]naphthalen-7-yl ester
CAS No.:88412-18-4
Molecular Formula:C₂₄H₃₆O₇Si
Molecular Weight:464.631
Hs Code.:

Acetic acid (3aS,5R,6S,7R,7aR)-6-benzyloxy-5-(tert-butyl-dimethyl-silanyloxymethyl)-hexahydro-1,3,4-trioxa-cyclopropa[a]naphthalen-7-yl ester

Synonyms:Acetic acid (3aS,5R,6S,7R,7aR)-6-benzyloxy-5-(tert-butyl-dimethyl-silanyloxymethyl)-hexahydro-1,3,4-trioxa-cyclopropa[a]naphthalen-7-yl ester

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Chemical Property of Acetic acid (3aS,5R,6S,7R,7aR)-6-benzyloxy-5-(tert-butyl-dimethyl-silanyloxymethyl)-hexahydro-1,3,4-trioxa-cyclopropa[a]naphthalen-7-yl ester

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Technology Process of Acetic acid (3aS,5R,6S,7R,7aR)-6-benzyloxy-5-(tert-butyl-dimethyl-silanyloxymethyl)-hexahydro-1,3,4-trioxa-cyclopropa[a]naphthalen-7-yl ester

There total 17 articles about Acetic acid (3aS,5R,6S,7R,7aR)-6-benzyloxy-5-(tert-butyl-dimethyl-silanyloxymethyl)-hexahydro-1,3,4-trioxa-cyclopropa[a]naphthalen-7-yl 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: 91.0%

: 88412-17-3
Acetic acid (2R,3S,4R,4aR,8aS)-3-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4,4a,8a-tetrahydro-2H,7H-pyrano[2,3-b]pyran-4-yl ester

: 88412-18-4
Acetic acid (3aS,5R,6S,7R,7aR)-6-benzyloxy-5-(tert-butyl-dimethyl-silanyloxymethyl)-hexahydro-1,3,4-trioxa-cyclopropa[a]naphthalen-7-yl ester

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid;
DOI:10.1021/ja00315a046

Reference yield:

: 33208-47-8
4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose

: 88412-18-4,89824-77-1
Acetic acid (1aS,3aS,5R,6S,7R,7aR,7bR)-6-benzyloxy-5-(tert-butyl-dimethyl-silanyloxymethyl)-hexahydro-1,3,4-trioxa-cyclopropa[a]naphthalen-7-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) n-BuLi, 2.) Et₂AlCl

2: 99 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

3: H₂ / 5percent Pd/CaCO₃, lead oxide / ethyl acetate

4: 1.) trifluoroacetic acid, 2.) triethylamine, 4-(dimethylamino)pyridine / 1.) 0 deg C, 2 h, 2.) CH₂Cl₂, 25 deg C, 3 h

5: 41.4 mg / m-chloroperbenzoic acid / CHCl₃ / 26 h / 25 °C

6: 4-(dimethylamino)pyridine / ethyl acetate / Ambient temperature

With dmap; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; diethylaluminium chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; Lindlar catalyst; In tetrahydrofuran; chloroform; ethyl acetate;
DOI:10.1021/jo00229a013

Reference yield:

: 89731-34-0
1,6-anhydro-4-O-benzyl-2-deoxy-2-C-(3-hydroxypropynyl)-β-D-glucopyranose

: 88412-18-4,89824-77-1
Acetic acid (1aS,3aS,5R,6S,7R,7aR,7bR)-6-benzyloxy-5-(tert-butyl-dimethyl-silanyloxymethyl)-hexahydro-1,3,4-trioxa-cyclopropa[a]naphthalen-7-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: H₂ / 5percent Pd/CaCO₃, lead oxide / ethyl acetate

2: 1.) trifluoroacetic acid, 2.) triethylamine, 4-(dimethylamino)pyridine / 1.) 0 deg C, 2 h, 2.) CH₂Cl₂, 25 deg C, 3 h

3: 41.4 mg / m-chloroperbenzoic acid / CHCl₃ / 26 h / 25 °C

4: 4-(dimethylamino)pyridine / ethyl acetate / Ambient temperature

With dmap; hydrogen; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; Lindlar catalyst; In chloroform; ethyl acetate;
DOI:10.1021/jo00229a013