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

Base Information

Chemical Name:(2R,3R)-2-[(1R)-1-[(tert-butyldimethylsilyl)oxy]-1-(2-methoxy-4,5-methylenedioxyphenyl)methyl]-3-[(tert-butyldiphenylsilyl)oxy]methyl-1,4-butanediol
CAS No.:251940-63-3
Molecular Formula:C₃₆H₅₂O₇Si₂
Molecular Weight:652.976
Hs Code.:

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

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

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

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

There total 7 articles about (2R,3R)-2-[(1R)-1-[(tert-butyldimethylsilyl)oxy]-1-(2-methoxy-4,5-methylenedioxyphenyl)methyl]-3-[(tert-butyldiphenylsilyl)oxy]methyl-1,4-butanediol 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%

: 251940-61-1
(3S,4R)-3-[(1R)-1-[(tert-butyldimethylsilyl)oxy]-1-(2-methoxy-4,5-methylenedioxyphenyl)methyl]-4-[(tert-butyldiphenylsilyl)oxy]methyldihydro-2(3H)-furanone

: 251940-63-3
(2R,3R)-2-[(1R)-1-[(tert-butyldimethylsilyl)oxy]-1-(2-methoxy-4,5-methylenedioxyphenyl)methyl]-3-[(tert-butyldiphenylsilyl)oxy]methyl-1,4-butanediol

Guidance literature:: (3S,4R)-3-[(1R)-1-[(tert-butyldimethylsilyl)oxy]-1-(2-methoxy-4,5-methylenedioxyphenyl)methyl]-4-[(tert-butyldiphenylsilyl)oxy]methyldihydro-2(3H)-furanone; With diisobutylaluminium hydride; In toluene; at -75 ℃; for 0.5h;

With sodium tetrahydroborate; In ethanol; at 20 ℃; for 1h;
DOI:10.1271/bbb.63.1605

Reference yield:

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

: 251940-63-3
(2R,3R)-2-[(1R)-1-[(tert-butyldimethylsilyl)oxy]-1-(2-methoxy-4,5-methylenedioxyphenyl)methyl]-3-[(tert-butyldiphenylsilyl)oxy]methyl-1,4-butanediol

Guidance literature:: Multi-step reaction with 4 steps

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

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

3.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

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

4.2: 91 percent / NaBH₄ / ethanol / 1 h / 20 °C

With 2,6-dimethylpyridine; 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;
DOI:10.1271/bbb.63.1605

Reference yield:

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

: 251940-63-3
(2R,3R)-2-[(1R)-1-[(tert-butyldimethylsilyl)oxy]-1-(2-methoxy-4,5-methylenedioxyphenyl)methyl]-3-[(tert-butyldiphenylsilyl)oxy]methyl-1,4-butanediol

Guidance literature:: Multi-step reaction with 3 steps

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

2.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

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

3.2: 91 percent / NaBH₄ / ethanol / 1 h / 20 °C

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