Benzoic acid (2R,3R,4R,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-6-isopropoxy-3-methyl-tetrahydro-pyran-4-yl ester

Base Information

Chemical Name:Benzoic acid (2R,3R,4R,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-6-isopropoxy-3-methyl-tetrahydro-pyran-4-yl ester
CAS No.:524734-65-4
Molecular Formula:C₂₃H₃₈O₆Si
Molecular Weight:438.637
Hs Code.:

Synonyms:Benzoic acid (2R,3R,4R,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-6-isopropoxy-3-methyl-tetrahydro-pyran-4-yl ester

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Chemical Property of Benzoic acid (2R,3R,4R,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-6-isopropoxy-3-methyl-tetrahydro-pyran-4-yl ester

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Technology Process of Benzoic acid (2R,3R,4R,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-6-isopropoxy-3-methyl-tetrahydro-pyran-4-yl ester

There total 8 articles about Benzoic acid (2R,3R,4R,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-6-isopropoxy-3-methyl-tetrahydro-pyran-4-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: 94.0%

: 98-88-4
benzoyl chloride

: 524734-64-3
(2R,3R,4R,6S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-6-isopropoxy-3-methyl-tetrahydro-pyran-3,4-diol

: 524734-65-4
Benzoic acid (2R,3R,4R,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-6-isopropoxy-3-methyl-tetrahydro-pyran-4-yl ester

Guidance literature:: With pyridine; In dichloromethane; at 20 ℃; for 7h;
DOI:10.1021/jo034021y

Reference yield:

: 23339-26-6,56196-34-0
isopropyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

: 524734-65-4
Benzoic acid (2R,3R,4R,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-6-isopropoxy-3-methyl-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 100 percent / imidazole / dimethylformamide / 0.5 h / 0 °C

2.1: 97 percent / Ac₂O / dimethylsulfoxide / 11.5 h / 20 °C

3.1: n-BuLi / tetrahydrofuran / 0.5 h / 20 °C

3.2: 81 percent / tetrahydrofuran / 2.5 h / -78 - 20 °C

4.1: 79 percent / Li; liquid NH₃ / ethanol / 0.5 h / Heating

5.1: 74 percent / AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 25.5 h / 20 °C

6.1: 94 percent / pyridine / CH₂Cl₂ / 7 h / 20 °C

With pyridine; 1H-imidazole; n-butyllithium; methanesulfonamide; AD-mix-β; ammonia; acetic anhydride; lithium; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/jo034021y

Reference yield:

: 69247-19-4,113019-32-2,23339-23-3
isopropyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

: 524734-65-4
Benzoic acid (2R,3R,4R,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-6-isopropoxy-3-methyl-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 116.5 g / Et₃N / methanol; H₂O / 5.5 h / 20 °C

2.1: 100 percent / imidazole / dimethylformamide / 0.5 h / 0 °C

3.1: 97 percent / Ac₂O / dimethylsulfoxide / 11.5 h / 20 °C

4.1: n-BuLi / tetrahydrofuran / 0.5 h / 20 °C

4.2: 81 percent / tetrahydrofuran / 2.5 h / -78 - 20 °C

5.1: 79 percent / Li; liquid NH₃ / ethanol / 0.5 h / Heating

6.1: 74 percent / AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 25.5 h / 20 °C

7.1: 94 percent / pyridine / CH₂Cl₂ / 7 h / 20 °C

With pyridine; 1H-imidazole; n-butyllithium; methanesulfonamide; AD-mix-β; ammonia; acetic anhydride; lithium; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/jo034021y