ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside

Base Information

Chemical Name:ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside
CAS No.:289057-09-6
Molecular Formula:C₂₈H₄₀O₅SSi
Molecular Weight:516.774
Hs Code.:

Synonyms:ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside

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Chemical Property of ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside

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Technology Process of ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside

There total 5 articles about ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside 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: 90.0%

: 100-39-0
benzyl bromide

: 153185-20-7
ethyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside

: 289057-09-6
ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 2h; Inert atmosphere;
DOI:10.1039/d1ob00188d

Reference yield:

: 4163-65-9
per-O-acetyl-α-D-mannopyranose

: 289057-09-6
ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

2.1: sodium methylate; methanol / 1 h / 20 °C / pH Ca_. 9

3.1: camphor-10-sulfonic acid / acetonitrile / 0.5 h / 20 °C

4.1: di(n-butyl)tin oxide / methanol / 0.5 h / Reflux

4.2: 2 h / 20 °C / Inert atmosphere

5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / 0 °C / Inert atmosphere

With methanol; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium methylate; sodium hydride; di(n-butyl)tin oxide; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; mineral oil;
DOI:10.1039/d1ob00188d

Reference yield:

: 32934-24-0,41670-79-5,52645-73-5,55722-49-1,79389-52-9,99031-86-4,125354-48-5,126187-25-5
S-ethyl 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside

: 289057-09-6
ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium methylate; methanol / 1 h / 20 °C / pH Ca_. 9

2.1: camphor-10-sulfonic acid / acetonitrile / 0.5 h / 20 °C

3.1: di(n-butyl)tin oxide / methanol / 0.5 h / Reflux

3.2: 2 h / 20 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / 0 °C / Inert atmosphere

With methanol; camphor-10-sulfonic acid; sodium methylate; sodium hydride; di(n-butyl)tin oxide; In methanol; N,N-dimethyl-formamide; acetonitrile; mineral oil;
DOI:10.1039/d1ob00188d