(2R,3R)-1,4-diacetoxy-2-[(1S)-1-[(tert-butyldimethylsilyl)oxy]-1-(2-methoxy-4,5-methylenedioxyphenyl)methyl]-3-[(tert-butyldiphenylsilyl)oxy]methylbutane

Base Information

Chemical Name:(2R,3R)-1,4-diacetoxy-2-[(1S)-1-[(tert-butyldimethylsilyl)oxy]-1-(2-methoxy-4,5-methylenedioxyphenyl)methyl]-3-[(tert-butyldiphenylsilyl)oxy]methylbutane
CAS No.:251940-64-4
Molecular Formula:C₄₀H₅₆O₉Si₂
Molecular Weight:737.05
Hs Code.:

(2R,3R)-1,4-diacetoxy-2-[(1S)-1-[(tert-butyldimethylsilyl)oxy]-1-(2-methoxy-4,5-methylenedioxyphenyl)methyl]-3-[(tert-butyldiphenylsilyl)oxy]methylbutane

Synonyms:(2R,3R)-1,4-diacetoxy-2-[(1S)-1-[(tert-butyldimethylsilyl)oxy]-1-(2-methoxy-4,5-methylenedioxyphenyl)methyl]-3-[(tert-butyldiphenylsilyl)oxy]methylbutane

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Chemical Property of (2R,3R)-1,4-diacetoxy-2-[(1S)-1-[(tert-butyldimethylsilyl)oxy]-1-(2-methoxy-4,5-methylenedioxyphenyl)methyl]-3-[(tert-butyldiphenylsilyl)oxy]methylbutane

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Technology Process of (2R,3R)-1,4-diacetoxy-2-[(1S)-1-[(tert-butyldimethylsilyl)oxy]-1-(2-methoxy-4,5-methylenedioxyphenyl)methyl]-3-[(tert-butyldiphenylsilyl)oxy]methylbutane

There total 8 articles about (2R,3R)-1,4-diacetoxy-2-[(1S)-1-[(tert-butyldimethylsilyl)oxy]-1-(2-methoxy-4,5-methylenedioxyphenyl)methyl]-3-[(tert-butyldiphenylsilyl)oxy]methylbutane 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: 96.0%

: 108-24-7
acetic anhydride

: 251940-62-2
(2R,3R)-2-[(1S)-1-[(tert-butyldimethylsilyl)oxy]-1-(2-methoxy-4,5-methylenedioxyphenyl)methyl]-3-[(tert-butyldiphenylsilyl)oxy]methyl-1,4-butanediol

: 251940-64-4
(2R,3R)-1,4-diacetoxy-2-[(1S)-1-[(tert-butyldimethylsilyl)oxy]-1-(2-methoxy-4,5-methylenedioxyphenyl)methyl]-3-[(tert-butyldiphenylsilyl)oxy]methylbutane

Guidance literature:: With dmap; at 20 ℃; for 18h;
DOI:10.1271/bbb.63.1605

Reference yield:

: 201804-35-5
(4R)-4-[(tert-butyldiphenylsilyl)oxy]methyldihydro-2(3H)-furanone

: 251940-64-4
(2R,3R)-1,4-diacetoxy-2-[(1S)-1-[(tert-butyldimethylsilyl)oxy]-1-(2-methoxy-4,5-methylenedioxyphenyl)methyl]-3-[(tert-butyldiphenylsilyl)oxy]methylbutane

Guidance literature:: Multi-step reaction with 4 steps

1.1: 43 percent / LDA / tetrahydrofuran / 2 h / -75 °C

2.1: 82 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

3.1: DIBAL-H / toluene / 0.5 h / -75 °C

3.2: 100 percent / NaBH₄ / ethanol / 1 h / 20 °C

4.1: 96 percent / DMAP / 18 h / 20 °C

With 2,6-dimethylpyridine; dmap; diisobutylaluminium hydride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene; 1.1: Condensation / 2.1: silylation / 3.1: Reduction / 3.2: Reduction / 4.1: Acetylation;
DOI:10.1271/bbb.63.1605

Reference yield:

: 251940-57-5
(2R/S,4R)-4-[(tert-butyldiphenylsilyl)oxy]methyl-2-hydroxytetrahydrofuran

: 251940-64-4
(2R,3R)-1,4-diacetoxy-2-[(1S)-1-[(tert-butyldimethylsilyl)oxy]-1-(2-methoxy-4,5-methylenedioxyphenyl)methyl]-3-[(tert-butyldiphenylsilyl)oxy]methylbutane

Guidance literature:: Multi-step reaction with 5 steps

1.1: 87 percent / Ag₃CO₃-Celite / toluene / 0.5 h / Heating

2.1: 43 percent / LDA / tetrahydrofuran / 2 h / -75 °C

3.1: 82 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

4.1: DIBAL-H / toluene / 0.5 h / -75 °C

4.2: 100 percent / NaBH₄ / ethanol / 1 h / 20 °C

5.1: 96 percent / DMAP / 18 h / 20 °C

With 2,6-dimethylpyridine; dmap; diisobutylaluminium hydride; silver carbonate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene; 1.1: Oxidation / 2.1: Condensation / 3.1: silylation / 4.1: Reduction / 4.2: Reduction / 5.1: Acetylation;
DOI:10.1271/bbb.63.1605