Benzoic acid (Z)-(1R,3S,4S)-3,8-bis-benzyloxy-6-benzyloxymethyl-1-methyl-5-methylene-2-oxo-4-triethylsilanyloxy-oct-6-enyl ester

Base Information

Chemical Name:Benzoic acid (Z)-(1R,3S,4S)-3,8-bis-benzyloxy-6-benzyloxymethyl-1-methyl-5-methylene-2-oxo-4-triethylsilanyloxy-oct-6-enyl ester
CAS No.:185757-69-1
Molecular Formula:C₄₅H₅₄O₇Si
Molecular Weight:735.005
Hs Code.:

Synonyms:Benzoic acid (Z)-(1R,3S,4S)-3,8-bis-benzyloxy-6-benzyloxymethyl-1-methyl-5-methylene-2-oxo-4-triethylsilanyloxy-oct-6-enyl ester

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Chemical Property of Benzoic acid (Z)-(1R,3S,4S)-3,8-bis-benzyloxy-6-benzyloxymethyl-1-methyl-5-methylene-2-oxo-4-triethylsilanyloxy-oct-6-enyl ester

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Technology Process of Benzoic acid (Z)-(1R,3S,4S)-3,8-bis-benzyloxy-6-benzyloxymethyl-1-methyl-5-methylene-2-oxo-4-triethylsilanyloxy-oct-6-enyl ester

There total 7 articles about Benzoic acid (Z)-(1R,3S,4S)-3,8-bis-benzyloxy-6-benzyloxymethyl-1-methyl-5-methylene-2-oxo-4-triethylsilanyloxy-oct-6-enyl 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: 76.0%

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: 185757-68-0
Benzoic acid (Z)-(1R,3S,4S)-3,8-bis-benzyloxy-6-benzyloxymethyl-4-hydroxy-1-methyl-5-methylene-2-oxo-oct-6-enyl ester

: 185757-69-1
Benzoic acid (Z)-(1R,3S,4S)-3,8-bis-benzyloxy-6-benzyloxymethyl-1-methyl-5-methylene-2-oxo-4-triethylsilanyloxy-oct-6-enyl ester

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1016/S0040-4039(96)02083-7

Reference yield:

: 68972-96-3
(Z)-1,4-dibenzyloxy-2-butene

: 185757-69-1
Benzoic acid (Z)-(1R,3S,4S)-3,8-bis-benzyloxy-6-benzyloxymethyl-1-methyl-5-methylene-2-oxo-4-triethylsilanyloxy-oct-6-enyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: I₂ / CH₂Cl₂

2: 1.) n-BuLi, 2.) ZnBr₂, 3.) Pd(MeCN)2Cl₂ / 1.) THF, -78 deg C, 30 min, 2.) 2.5 h, 3.) DMF, from -78 deg C to 20 deg C, 2 h

3: 1M HCl / tetrahydrofuran / 4 h / 20 °C

4: 1.) (c-C₆H₁₁)2BCl, Et₃N, Me₂NEt, 3.) H₂O₂ / 1.) Et₂O, 0 deg C, 3 h, 2.) from -78 deg C to -18 deg C, 18 h, 3.) MeOH, pH 7 buffer

5: 76 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

With 2,6-dimethylpyridine; hydrogenchloride; dichloro bis(acetonitrile) palladium(II); n-butyllithium; N,N-dimethyl-ethanamine; dicyclohexylboron chloride; dihydrogen peroxide; iodine; triethylamine; zinc dibromide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4039(96)02083-7

Reference yield:

: 93877-21-5
1,4-dibenzyloxybut-2-yne

: 185757-69-1
Benzoic acid (Z)-(1R,3S,4S)-3,8-bis-benzyloxy-6-benzyloxymethyl-1-methyl-5-methylene-2-oxo-4-triethylsilanyloxy-oct-6-enyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: Bu₃SnH, Pd(PPh₃)4 / tetrahydrofuran

2: I₂ / CH₂Cl₂

3: 1.) n-BuLi, 2.) ZnBr₂, 3.) Pd(MeCN)2Cl₂ / 1.) THF, -78 deg C, 30 min, 2.) 2.5 h, 3.) DMF, from -78 deg C to 20 deg C, 2 h

4: 1M HCl / tetrahydrofuran / 4 h / 20 °C

5: 1.) (c-C₆H₁₁)2BCl, Et₃N, Me₂NEt, 3.) H₂O₂ / 1.) Et₂O, 0 deg C, 3 h, 2.) from -78 deg C to -18 deg C, 18 h, 3.) MeOH, pH 7 buffer

6: 76 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

With 2,6-dimethylpyridine; hydrogenchloride; dichloro bis(acetonitrile) palladium(II); tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; N,N-dimethyl-ethanamine; dicyclohexylboron chloride; dihydrogen peroxide; iodine; tri-n-butyl-tin hydride; triethylamine; zinc dibromide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4039(96)02083-7