(2R,3R,4S,5R,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl acetate

Base Information

Chemical Name:(2R,3R,4S,5R,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl acetate
CAS No.:1442690-55-2
Molecular Formula:C₁₅H₂₀O₆
Molecular Weight:296.32
Hs Code.:

Synonyms:(2R,3R,4S,5R,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl acetate

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Chemical Property of (2R,3R,4S,5R,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl acetate

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Technology Process of (2R,3R,4S,5R,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl acetate

There total 6 articles about (2R,3R,4S,5R,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl acetate 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: 92.0%

: 1451866-16-2
(2R,3R,6S)-2-(benzyloxy)-6-methyl-3,6-dihydro-2H-pyran-3-yl acetate

: 1442690-55-2
(2R,3R,4S,5R,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl acetate

Guidance literature:: With osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; In acetone; tert-butyl alcohol; at 0 ℃;
DOI:10.1002/ejoc.201300051

Reference yield:

: 865484-73-7
tert-butyl ((2S,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate

: 1442690-55-2
(2R,3R,4S,5R,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl acetate

Guidance literature:: Multi-step reaction with 5 steps

1: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenylphosphine

2: dihydrogen peroxide; sodium hydroxide

3: hydrazine hydrate

4: pyridine / 0 °C

5: osmium(VIII) oxide; 4-methylmorpholine N-oxide; water / tert-butyl alcohol; acetone / 0 °C

With pyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; osmium(VIII) oxide; water; dihydrogen peroxide; hydrazine hydrate; 4-methylmorpholine N-oxide; triphenylphosphine; sodium hydroxide; In acetone; tert-butyl alcohol; 3: |Wharton Fragmentation / 3: |Wharton Fragmentation;
DOI:10.1002/ejoc.201300051

Reference yield:

: 512809-21-1
benzyl 2,3,6-trideoxy-α-L-hex-2-enopyranosid-4-ulose

: 1442690-55-2
(2R,3R,4S,5R,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl acetate

Guidance literature:: Multi-step reaction with 4 steps

1: dihydrogen peroxide; sodium hydroxide

2: hydrazine hydrate

3: pyridine / 0 °C

4: osmium(VIII) oxide; 4-methylmorpholine N-oxide; water / tert-butyl alcohol; acetone / 0 °C

With pyridine; osmium(VIII) oxide; water; dihydrogen peroxide; hydrazine hydrate; 4-methylmorpholine N-oxide; sodium hydroxide; In acetone; tert-butyl alcohol; 2: |Wharton Fragmentation / 2: |Wharton Fragmentation;
DOI:10.1002/ejoc.201300051