(2S,5R,6S)-2-(1-tert-butyldiphenylsilyl)oxymethyl-5-acetoxy-6-decyl-3,4-dihydropyran

Base Information

Chemical Name:(2S,5R,6S)-2-(1-tert-butyldiphenylsilyl)oxymethyl-5-acetoxy-6-decyl-3,4-dihydropyran
CAS No.:220772-66-7
Molecular Formula:C₃₄H₅₀O₄Si
Molecular Weight:550.854
Hs Code.:

Synonyms:(2S,5R,6S)-2-(1-tert-butyldiphenylsilyl)oxymethyl-5-acetoxy-6-decyl-3,4-dihydropyran

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Chemical Property of (2S,5R,6S)-2-(1-tert-butyldiphenylsilyl)oxymethyl-5-acetoxy-6-decyl-3,4-dihydropyran

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Technology Process of (2S,5R,6S)-2-(1-tert-butyldiphenylsilyl)oxymethyl-5-acetoxy-6-decyl-3,4-dihydropyran

There total 13 articles about (2S,5R,6S)-2-(1-tert-butyldiphenylsilyl)oxymethyl-5-acetoxy-6-decyl-3,4-dihydropyran 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: 66.0%

: 108-24-7
acetic anhydride

: 220772-65-6
(2R,3R,4S,5R,6S)-2-(1-tert-butyldiphenylsilyl)oxymethyl-3,4,5-trihydroxy-6-decyltetrahydropyran

: 220772-66-7
(2S,5R,6S)-2-(1-tert-butyldiphenylsilyl)oxymethyl-5-acetoxy-6-decyl-3,4-dihydropyran

Guidance literature:: (2R,3R,4S,5R,6S)-2-(1-tert-butyldiphenylsilyl)oxymethyl-3,4,5-trihydroxy-6-decyltetrahydropyran; With (1S)-10-camphorsulfonic acid; trimethyl orthoformate; In dichloromethane; at 20 ℃; for 3h;

acetic anhydride; at 130 ℃; for 7h; Further stages.;
DOI:10.1021/jo020211h

Reference yield:

: 17049-50-2
n-decyl magnesium bromide

: 220772-66-7
(2S,5R,6S)-2-(1-tert-butyldiphenylsilyl)oxymethyl-5-acetoxy-6-decyl-3,4-dihydropyran

Guidance literature:: Multi-step reaction with 5 steps

1.1: diethyl ether / 2.5 h / -78 °C

2.1: 1.17 g / triethylsilane; BF₃*Et₂O / CH₂Cl₂ / 3.5 h / -40 - -30 °C

3.1: hydrogen / 10percent Pd/C / methanol; ethyl acetate / 96 h / 20 °C

4.1: 10.4 g / imidazole / dimethylformamide / 18 h / 20 °C

5.1: trimethyl orthoformate; d-camphorsulfonic acid / CH₂Cl₂ / 3 h / 20 °C

5.2: 66 percent / 7 h / 130 °C

With 1H-imidazole; triethylsilane; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; hydrogen; trimethyl orthoformate; 10percent Pd/C; In methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo020211h

Reference yield:

: 82598-84-3
2,3,4,6-tetra-O-benzyl-D-galactonolactone

: 220772-66-7
(2S,5R,6S)-2-(1-tert-butyldiphenylsilyl)oxymethyl-5-acetoxy-6-decyl-3,4-dihydropyran

Guidance literature:: Multi-step reaction with 5 steps

1.1: diethyl ether / 2.5 h / -78 °C

2.1: 1.17 g / triethylsilane; BF₃*Et₂O / CH₂Cl₂ / 3.5 h / -40 - -30 °C

3.1: hydrogen / 10percent Pd/C / methanol; ethyl acetate / 96 h / 20 °C

4.1: 10.4 g / imidazole / dimethylformamide / 18 h / 20 °C

5.1: trimethyl orthoformate; d-camphorsulfonic acid / CH₂Cl₂ / 3 h / 20 °C

5.2: 66 percent / 7 h / 130 °C

With 1H-imidazole; triethylsilane; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; hydrogen; trimethyl orthoformate; 10percent Pd/C; In methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo020211h