methyl 6-O-tert-butyldimethylsilyl-3,5-O-isopropylidene-2-deoxy-2-benzylthio-α-D-glucofuranoside

Base Information

Chemical Name:methyl 6-O-tert-butyldimethylsilyl-3,5-O-isopropylidene-2-deoxy-2-benzylthio-α-D-glucofuranoside
CAS No.:1426261-84-8
Molecular Formula:C₂₃H₃₈O₅SSi
Molecular Weight:454.703
Hs Code.:

Synonyms:methyl 6-O-tert-butyldimethylsilyl-3,5-O-isopropylidene-2-deoxy-2-benzylthio-α-D-glucofuranoside

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Chemical Property of methyl 6-O-tert-butyldimethylsilyl-3,5-O-isopropylidene-2-deoxy-2-benzylthio-α-D-glucofuranoside

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Technology Process of methyl 6-O-tert-butyldimethylsilyl-3,5-O-isopropylidene-2-deoxy-2-benzylthio-α-D-glucofuranoside

There total 3 articles about methyl 6-O-tert-butyldimethylsilyl-3,5-O-isopropylidene-2-deoxy-2-benzylthio-α-D-glucofuranoside 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: 62.0%

: 123620-00-8
(4R,5R)-5-{[(tert-butyldimethylsilyl)oxy]methyl}-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

: trans-1-methoxy-2-benzylmercaptoethylene

: 1426261-84-8
methyl 6-O-tert-butyldimethylsilyl-3,5-O-isopropylidene-2-deoxy-2-benzylthio-α-D-glucofuranoside

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 2h; diastereoselective reaction; Inert atmosphere;
DOI:10.1055/s-0032-1317860

Reference yield:

: 100-53-8
phenylmethanethiol

: 1426261-84-8
methyl 6-O-tert-butyldimethylsilyl-3,5-O-isopropylidene-2-deoxy-2-benzylthio-α-D-glucofuranoside

Guidance literature:: Multi-step reaction with 3 steps

1: sodium hydride / tetrahydrofuran / 0 - 20 °C

2: n-butyllithium / tetrahydrofuran / -78 °C

3: boron trifluoride diethyl etherate / dichloromethane / 2 h / -78 °C / Inert atmosphere

With n-butyllithium; boron trifluoride diethyl etherate; sodium hydride; In tetrahydrofuran; dichloromethane;
DOI:10.1055/s-0032-1317860

Reference yield:

: 6304-94-5
benzylmercaptoacetaldehyde dimethyl acetal

: 1426261-84-8
methyl 6-O-tert-butyldimethylsilyl-3,5-O-isopropylidene-2-deoxy-2-benzylthio-α-D-glucofuranoside

Guidance literature:: Multi-step reaction with 2 steps

1: n-butyllithium / tetrahydrofuran / -78 °C

2: boron trifluoride diethyl etherate / dichloromethane / 2 h / -78 °C / Inert atmosphere

With n-butyllithium; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane;
DOI:10.1055/s-0032-1317860