(2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-3-hydroxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-3-hydroxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
CAS No.:211678-07-8
Molecular Formula:C₂₆H₃₆O₇Si
Molecular Weight:488.653
Hs Code.:

Synonyms:(2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-3-hydroxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

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Chemical Property of (2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-3-hydroxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

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Technology Process of (2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-3-hydroxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 10 articles about (2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-3-hydroxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 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: 81.0%

: 211678-06-7
(2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-3-hydroxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid

: 18107-18-1
diazomethyl-trimethyl-silane

: 211678-07-8
(2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-3-hydroxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: In methanol; hexane; for 0.5h;
DOI:10.1016/S0008-6215(98)00020-2

Reference yield:

: methyl (2-(trimethylsilyl)ethyl 2-O-benzyl-exo-3,4-O-benzylidene-β-D-galactopyranoside)uronate

: methyl (2-(trimethylsilyl)ethyl 2,4-di-O-benzyl-β-D-galactopyranoside)uronate

: 211678-07-8
(2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-3-hydroxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: With borane-THF; di-n-butylboryl trifluoromethanesulfonate; In toluene; at 0 ℃; for 2h; Overall yield = 81 %; Overall yield = 40 mg;
DOI:10.1139/cjc-2016-0006

Reference yield:

: 191924-41-1
2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-β-D-galactopyranoside

: 211678-07-8
(2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-3-hydroxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 54 percent / 2,2,6,6-tetramethylpiperidinyloxy radical, KBr, Bu₄NBr, aq NaOCl, sat aq NaHCO₃, sat aq NaCl / CH₂Cl₂ / 1.67 h / 0 °C

2: 81 percent / methanol; hexane / 0.5 h

With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutylammomium bromide; sodium hydrogencarbonate; sodium chloride; potassium bromide; In methanol; hexane; dichloromethane;
DOI:10.1016/S0008-6215(98)00020-2