(3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-methoxy-2-methylene-tetrahydro-pyran-3-ol

Base Information

Chemical Name:(3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-methoxy-2-methylene-tetrahydro-pyran-3-ol
CAS No.:118068-40-9
Molecular Formula:C₂₁H₂₄O₅
Molecular Weight:356.419
Hs Code.:

Synonyms:(3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-methoxy-2-methylene-tetrahydro-pyran-3-ol

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Chemical Property of (3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-methoxy-2-methylene-tetrahydro-pyran-3-ol

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Technology Process of (3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-methoxy-2-methylene-tetrahydro-pyran-3-ol

There total 8 articles about (3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-methoxy-2-methylene-tetrahydro-pyran-3-ol 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:

: 118068-39-6
methyl 2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-altropyranoside

: 118068-40-9
(3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-methoxy-2-methylene-tetrahydro-pyran-3-ol

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 80 ℃; for 23h;
DOI:10.1021/jo00009a009 DOI:10.1246/cl.1988.969

Reference yield:

: 33164-03-3
methyl 2,3-di-O-benzyl-α-D-altropyranoside

: 118068-40-9
(3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-methoxy-2-methylene-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 74 percent / MeI, Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 19 h / Ambient temperature

2: DBU / toluene / 23 h / 80 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; diethylazodicarboxylate; methyl iodide; In tetrahydrofuran; toluene;
DOI:10.1246/cl.1988.969

Reference yield:

: 100-44-7
benzyl chloride

: 118068-40-9
(3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-methoxy-2-methylene-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) NaOH / 1.) H₂O, reflux, 48 h, 2.) DMSO, RT, 3 h

2: 100 percent / 80percent aq. HOAc / 0.5 h / 80 °C

3: 74 percent / diethyl azodicarboxylate, triphenylphosphine, CH₃I / tetrahydrofuran / 19 h / Ambient temperature

4: DBU / toluene / 23 h / 80 °C

With sodium hydroxide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; diethylazodicarboxylate; methyl iodide; In tetrahydrofuran; toluene;
DOI:10.1021/jo00009a009