(tert-butyldimethyl)silyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranoside

Base Information

Chemical Name:(tert-butyldimethyl)silyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranoside
CAS No.:230620-33-4
Molecular Formula:C₂₀H₃₁N₃O₅Si
Molecular Weight:421.569
Hs Code.:

Synonyms:(tert-butyldimethyl)silyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (tert-butyldimethyl)silyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranoside

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Technology Process of (tert-butyldimethyl)silyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranoside

There total 1 articles about (tert-butyldimethyl)silyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranoside 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: 97.0%

: 147254-13-5
(tert-butyldimethyl)silyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

: 74-88-4
methyl iodide

: 230620-33-4
(tert-butyldimethyl)silyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranoside

Guidance literature:: (tert-butyldimethyl)silyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

methyl iodide; In N,N-dimethyl-formamide; at 0 ℃; for 0.25h;
DOI:10.1139/v99-056

Reference yield:

: 230620-33-4
(tert-butyldimethyl)silyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranoside

: 2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-D-galactopyranose

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; at -25 ℃; for 0.166667h;
DOI:10.1139/v99-056

Reference yield:

: 230620-33-4
(tert-butyldimethyl)silyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranoside

: 230620-43-6
1-O-(2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranosyl) 2,3,4-tri-O-benzyl-L-ribitol

Guidance literature:: Multi-step reaction with 3 steps

1: Bu₄NF / CH₂Cl₂; tetrahydrofuran / 0.17 h / -25 °C

2: 69 percent / NaH / CH₂Cl₂ / 1 h / 0 °C

3: 16 percent / TMSOTf / acetonitrile / 0.67 h / -50 °C

With trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; dichloromethane; acetonitrile; 1: desilylation / 2: Addition / 3: glycosylation;
DOI:10.1139/v99-056