(2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-carboxylic acid tert-butyl ester
CAS No.:676241-05-7
Molecular Formula:C₃₂H₃₈O₇
Molecular Weight:534.65
Hs Code.:

Synonyms:(2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-carboxylic acid tert-butyl ester

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Chemical Property of (2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-carboxylic acid tert-butyl ester

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Technology Process of (2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-carboxylic acid tert-butyl ester

There total 4 articles about (2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-carboxylic acid tert-butyl 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: 71.0%

: 676241-04-6
(2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-carboxylic acid tert-butyl ester

: 676241-05-7
(2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-carboxylic acid tert-butyl ester

Guidance literature:: (2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-carboxylic acid tert-butyl ester; With ozone; In dichloromethane; at -78 ℃; for 0.5h;

With sodium tetrahydroborate; In methanol; dichloromethane; at 20 ℃; for 20h; Further stages.;
DOI:10.1016/j.tetlet.2003.12.032

Reference yield:

: 112219-66-6
(2R,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-vinyltetrahydro-2H-pyran

: 676241-05-7
(2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -40 °C

2.1: sodium methylate / methanol / 20 h / 20 °C

3.1: acetic anhydride; pyridinium chlorochromate / dichloromethane / 48 h / 20 °C

4.1: ozone / dichloromethane / 0.5 h / -78 °C

4.2: NaBH₄ / 11; 15 / 20 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; acetic anhydride; ozone; pyridinium chlorochromate; In methanol; dichloromethane; 2.1: Zemplen deacetylation;
DOI:10.1016/j.tetlet.2003.12.032

Reference yield:

: 676241-03-5
((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-yl)-methanol

: 676241-05-7
(2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: acetic anhydride; pyridinium chlorochromate / dichloromethane / 48 h / 20 °C

2.1: ozone / dichloromethane / 0.5 h / -78 °C

2.2: NaBH₄ / 11; 15 / 20 h / 20 °C

With acetic anhydride; ozone; pyridinium chlorochromate; In dichloromethane;
DOI:10.1016/j.tetlet.2003.12.032