(2R,3R,4S,5R,6R)-4-Benzyloxy-2-hydroxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3,5-diol

Base Information

Chemical Name:(2R,3R,4S,5R,6R)-4-Benzyloxy-2-hydroxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3,5-diol
CAS No.:189144-50-1
Molecular Formula:C₁₈H₃₀O₆Si
Molecular Weight:370.518
Hs Code.:

Synonyms:(2R,3R,4S,5R,6R)-4-Benzyloxy-2-hydroxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3,5-diol

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Chemical Property of (2R,3R,4S,5R,6R)-4-Benzyloxy-2-hydroxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3,5-diol

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Technology Process of (2R,3R,4S,5R,6R)-4-Benzyloxy-2-hydroxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3,5-diol

There total 4 articles about (2R,3R,4S,5R,6R)-4-Benzyloxy-2-hydroxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3,5-diol 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: 99.0%

: 189144-49-8
Acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

: 189144-50-1
(2R,3R,4S,5R,6R)-4-Benzyloxy-2-hydroxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3,5-diol

Guidance literature:: With sodium methylate; In methanol; at 50 ℃; for 1.5h;
DOI:10.1021/jo962300y

Reference yield:

: 2916-68-9
2-(Trimethylsilyl)ethanol

: 189144-50-1
(2R,3R,4S,5R,6R)-4-Benzyloxy-2-hydroxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3,5-diol

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) sym-collidine, 4 Angstroem molecular sieves, 2.) AgOTf, 3.) Ac₂O, pyridine / 1) CH₂Cl₂, 23 deg C, 3 h; 2) CH₂Cl₂, 0 deg C, 3 h; 3) 23 deg C, 12 h

2: 99 percent / NaOMe / methanol / 1.5 h / 50 °C

With pyridine; 2,4,6-trimethyl-pyridine; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; acetic anhydride; In methanol;
DOI:10.1021/jo962300y

Reference yield:

: 39686-94-7,56632-47-4,65827-58-9,99202-62-7,99202-66-1,103082-79-7,103703-00-0,103703-01-1,118711-49-2,127853-23-0,139563-66-9
1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose

: 189144-50-1
(2R,3R,4S,5R,6R)-4-Benzyloxy-2-hydroxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3,5-diol

Guidance literature:: Multi-step reaction with 3 steps

1: 91 percent / α,α-dichloromethyl methyl ether, ZnCl2*Et2O / CH2Cl2 / 0.33 h / 23 °C

2: 1.) sym-collidine, 4 Angstroem molecular sieves, 2.) AgOTf, 3.) Ac₂O, pyridine / 1) CH₂Cl₂, 23 deg C, 3 h; 2) CH₂Cl₂, 0 deg C, 3 h; 3) 23 deg C, 12 h

3: 99 percent / NaOMe / methanol / 1.5 h / 50 °C

With pyridine; 2,4,6-trimethyl-pyridine; zinc chloride diethyl ether; Dichloromethyl methyl ether; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; acetic anhydride; In methanol; dichloromethane;
DOI:10.1021/jo962300y