[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-methanol

Base Information

Chemical Name:[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-methanol
CAS No.:436153-70-7
Molecular Formula:C₂₇H₄₀O₅Si
Molecular Weight:472.697
Hs Code.:

Synonyms:[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-methanol

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Chemical Property of [(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-methanol

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Technology Process of [(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-methanol

There total 9 articles about [(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-methanol 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: 96.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 632354-40-6
(2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-hydroxymethyltetrahydropyran-3-ol

: 436153-70-7
[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: With 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride; In dichloromethane; Inert atmosphere;
DOI:10.1021/jo302267f

Reference yield:

: (2R,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-carbaldehyde

: 436153-70-7
[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.333333h;
DOI:10.1021/ol025814u

Reference yield:

: 100-39-0
benzyl bromide

: 436153-70-7
[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: Multi-step reaction with 4 steps

1: KOt-Bu / tetrahydrofuran / 1 h / 20 °C

2: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 5 h / 20 °C

3: sodium periodate / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 1 h / 20 °C

4: 8.39 g / sodium borohydride / methanol / 0.33 h / 0 °C

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; potassium tert-butylate; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; water; tert-butyl alcohol;
DOI:10.1021/ol025814u