(2S,3S,4R,5S)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Base Information

Chemical Name:(2S,3S,4R,5S)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
CAS No.:194991-50-9
Molecular Formula:C₆H₁₂O₅
Molecular Weight:164.158
Hs Code.:

Synonyms:(2S,3S,4R,5S)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3S,4R,5S)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Chemical Property:

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Technology Process of (2S,3S,4R,5S)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

There total 8 articles about (2S,3S,4R,5S)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 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: 31.0%

: C₁₉H₄₆O₆Si₄

: 194991-50-9,53319-04-3
(2S,3S,4R,5S)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

: 71075-63-3
6-deoxy-D-glucitol

: 50-70-4
D-sorbitol

: 154-58-5,53319-04-3
1,5-anhydro-D-glucitol

Guidance literature:: C₁₉H₄₆O₆Si₄; With bis(pentafluorophenyl)borinic acid; 1,1,3,3-tetramethyldisilazane; In chloroform-d1; at 25 ℃; for 15h; Inert atmosphere; Glovebox;

In methanol; regioselective reaction; Inert atmosphere; Glovebox;
DOI:10.1002/anie.201708109

Reference yield:

: methyl β-D-tagatopyranoside

: 194991-50-9,53319-04-3
(2S,3S,4R,5S)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

: 71075-63-3
6-deoxy-D-glucitol

: 50-70-4
D-sorbitol

: 154-58-5,53319-04-3
1,5-anhydro-D-glucitol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1,1,1,3,3,3-hexamethyl-disilazane / dichloromethane / 25 °C

2.1: bis(pentafluorophenyl)borinic acid; 1,1,3,3-tetramethyldisilazane / chloroform-d1 / 15 h / 25 °C / Inert atmosphere; Glovebox

2.2: Dowex? / Inert atmosphere; Glovebox

With bis(pentafluorophenyl)borinic acid; 1,1,1,3,3,3-hexamethyl-disilazane; 1,1,3,3-tetramethyldisilazane; In chloroform-d1; dichloromethane;
DOI:10.1002/anie.201708109

Reference yield:

: 20197-42-6
tagatose (β-pyranose)

: 194991-50-9,53319-04-3
(2S,3S,4R,5S)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

: 71075-63-3
6-deoxy-D-glucitol

: 50-70-4
D-sorbitol

: 154-58-5,53319-04-3
1,5-anhydro-D-glucitol

Guidance literature:: Multi-step reaction with 3 steps

1.1: acetyl chloride / 96 h / 0 - 25 °C

2.1: 1,1,1,3,3,3-hexamethyl-disilazane / dichloromethane / 25 °C

3.1: bis(pentafluorophenyl)borinic acid; 1,1,3,3-tetramethyldisilazane / chloroform-d1 / 15 h / 25 °C / Inert atmosphere; Glovebox

3.2: Dowex? / Inert atmosphere; Glovebox

With bis(pentafluorophenyl)borinic acid; acetyl chloride; 1,1,1,3,3,3-hexamethyl-disilazane; 1,1,3,3-tetramethyldisilazane; In chloroform-d1; dichloromethane;
DOI:10.1002/anie.201708109