(2R,3S,4R)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydro-2H-pyran-3-ol

Base Information

Chemical Name:(2R,3S,4R)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydro-2H-pyran-3-ol
CAS No.:193360-22-4
Molecular Formula:C₂₉H₃₄O₄Si
Molecular Weight:474.672
Hs Code.:

Synonyms:(2R,3S,4R)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydro-2H-pyran-3-ol

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Chemical Property of (2R,3S,4R)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydro-2H-pyran-3-ol

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Technology Process of (2R,3S,4R)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydro-2H-pyran-3-ol

There total 1 articles about (2R,3S,4R)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydro-2H-pyran-3-ol 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:

: 87316-22-1
(2R,3S,4R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol

: 100-39-0
benzyl bromide

: 193360-22-4
(2R,3S,4R)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydro-2H-pyran-3-ol

Guidance literature:: With tetrabutylammomium bromide; di(n-butyl)tin oxide; Yield given. Multistep reaction; 1.) TolH, reflux, 4 h, 2.) TolH, 80 deg C, 18 h;
DOI:10.1016/S0040-4020(97)90389-6

Reference yield: 88.0%

: 193360-22-4
(2R,3S,4R)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydro-2H-pyran-3-ol

: 74-88-4
methyl iodide

: 193360-24-6
((2R,3S,4R)-4-Benzyloxy-3-methoxy-3,4-dihydro-2H-pyran-2-ylmethoxy)-tert-butyl-diphenyl-silane

Guidance literature:: With sodium hydride; In benzene; for 14h; Heating;
DOI:10.1016/S0040-4020(97)90389-6

Reference yield:

: 193360-22-4
(2R,3S,4R)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydro-2H-pyran-3-ol

: 193360-45-1
[(2S,3S,4S,5R,6R)-6-(3-Amino-propoxymethyl)-4-benzyloxy-3-iodo-5-methoxy-tetrahydro-pyran-2-yloxy]-acetic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 88 percent / NaH / benzene / 14 h / Heating

2: 75 percent / N-iodosuccinimide / CH₂Cl₂ / 3 h / Ambient temperature

3: 79 percent / TBAF / tetrahydrofuran / 10 h / Ambient temperature

4: 50 percent / NaH / CH₂Cl₂ / 14 h / Ambient temperature

5: 91 percent / PPh₃ / tetrahydrofuran; H₂O / 5 h / 65 °C

6: LiOH / tetrahydrofuran; H₂O / 4 h

With lithium hydroxide; N-iodo-succinimide; tetrabutyl ammonium fluoride; sodium hydride; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; benzene;
DOI:10.1016/S0040-4020(97)90389-6