(2R,3R,4S,5R,6R)-2-Allyl-4-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-3,5-diol

Base Information

Chemical Name:(2R,3R,4S,5R,6R)-2-Allyl-4-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-3,5-diol
CAS No.:203925-38-6
Molecular Formula:C₁₆H₂₂O₅
Molecular Weight:294.348
Hs Code.:

Synonyms:(2R,3R,4S,5R,6R)-2-Allyl-4-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-3,5-diol

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Chemical Property of (2R,3R,4S,5R,6R)-2-Allyl-4-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-3,5-diol

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Technology Process of (2R,3R,4S,5R,6R)-2-Allyl-4-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-3,5-diol

There total 3 articles about (2R,3R,4S,5R,6R)-2-Allyl-4-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-3,5-diol 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:

: 74410-51-8
methyl 4,6-O-benzylidene-3-O-benzyl-α-D-altropyranoside

: 203925-38-6
(2R,3R,4S,5R,6R)-2-Allyl-4-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-3,5-diol

Guidance literature:: Multi-step reaction with 3 steps

1: 91 percent / TsOH / methanol

2: acetonitrile / 2.5 h / 70 - 80 °C

3: TMSOTf / acetonitrile / 12 h / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; In methanol; acetonitrile;
DOI:10.1021/ja973287h

Reference yield:

: 194039-07-1
methyl 3-O-benzyl-α-D-altropyranoside

: 203925-38-6
(2R,3R,4S,5R,6R)-2-Allyl-4-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-3,5-diol

Guidance literature:: Multi-step reaction with 2 steps

1: acetonitrile / 2.5 h / 70 - 80 °C

2: TMSOTf / acetonitrile / 12 h / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile;
DOI:10.1021/ja973287h

Reference yield:

: (2S,3S,4R,5R,6R)-4-Benzyloxy-2-methoxy-3,5-bis-trimethylsilanyloxy-6-trimethylsilanyloxymethyl-tetrahydro-pyran

: 762-72-1
allyl-trimethyl-silane

: 203925-38-6
(2R,3R,4S,5R,6R)-2-Allyl-4-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-3,5-diol

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; for 12h; Yield given; Ambient temperature;
DOI:10.1021/ja973287h