methyl 2-O-acetyl-3-O-benzyl-5-O-tert-butyl(dimethyl)silyl-D-glucuronate di(ethylthio)acetal

Base Information

Chemical Name:methyl 2-O-acetyl-3-O-benzyl-5-O-tert-butyl(dimethyl)silyl-D-glucuronate di(ethylthio)acetal
CAS No.:875576-52-6
Molecular Formula:C₂₆H₄₄O₇S₂Si
Molecular Weight:560.849
Hs Code.:

Synonyms:methyl 2-O-acetyl-3-O-benzyl-5-O-tert-butyl(dimethyl)silyl-D-glucuronate di(ethylthio)acetal

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Chemical Property of methyl 2-O-acetyl-3-O-benzyl-5-O-tert-butyl(dimethyl)silyl-D-glucuronate di(ethylthio)acetal

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Technology Process of methyl 2-O-acetyl-3-O-benzyl-5-O-tert-butyl(dimethyl)silyl-D-glucuronate di(ethylthio)acetal

There total 6 articles about methyl 2-O-acetyl-3-O-benzyl-5-O-tert-butyl(dimethyl)silyl-D-glucuronate di(ethylthio)acetal 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: 98.0%

: 875576-43-5
(2R,3R)-3-acetoxy-2-benzyloxy-4,4-bis(ethylthio)butanal

: 150811-50-0
(E)-((2-((tert-butyldimethylsilyl)oxy)-1-methoxyvinyl)oxy)trimethylsilane

: 875576-52-6
methyl 2-O-acetyl-3-O-benzyl-5-O-tert-butyl(dimethyl)silyl-D-glucuronate di(ethylthio)acetal

Guidance literature:: (E)-((2-((tert-butyldimethylsilyl)oxy)-1-methoxyvinyl)oxy)trimethylsilane; With magnesium bromide; In toluene; at -78 ℃; for 0.5h;

(2R,3R)-3-acetoxy-2-benzyloxy-4,4-bis(ethylthio)butanal; In toluene; at -78 - 20 ℃;
DOI:10.1002/anie.200502742

Reference yield: 38.0%

: 875576-43-5
(2R,3R)-3-acetoxy-2-benzyloxy-4,4-bis(ethylthio)butanal

: 150811-50-0
(E)-((2-((tert-butyldimethylsilyl)oxy)-1-methoxyvinyl)oxy)trimethylsilane

: 875576-52-6
methyl 2-O-acetyl-3-O-benzyl-5-O-tert-butyl(dimethyl)silyl-D-glucuronate di(ethylthio)acetal

: 948039-10-9
methyl 2-O-acetyl-3-O-benzyl-5-O-tert-butyl(dimethyl)silyl-L-iduronate di(ethylthio)acetal

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 0.25h;
DOI:10.1002/anie.200502742

Reference yield:

: 875576-41-3
2-O-acetyl-3-O-benzyl-L-arabinose di(ethylthio)acetal

: 875576-52-6
methyl 2-O-acetyl-3-O-benzyl-5-O-tert-butyl(dimethyl)silyl-D-glucuronate di(ethylthio)acetal

Guidance literature:: Multi-step reaction with 2 steps

1.1: 80 percent / NaIO₄ / H₂O; tetrahydrofuran / 0.17 h / 0 °C

2.1: MgBr₂*Et₂O / toluene / 0.5 h / -78 °C

2.2: 98 percent / toluene / -78 - 20 °C

With sodium periodate; magnesium bromide; In tetrahydrofuran; water; toluene; 2.2: Felkin-Anh aldol reaction;
DOI:10.1002/anie.200502742