(1R,3S,4R,5R,6S)-5,6-dibenzyloxy-3-methoxy-4-methoxycarbonylmethyl-2-oxabicyclo<2.2.1>heptane

Base Information

Chemical Name:(1R,3S,4R,5R,6S)-5,6-dibenzyloxy-3-methoxy-4-methoxycarbonylmethyl-2-oxabicyclo<2.2.1>heptane
CAS No.:170953-36-3
Molecular Formula:C₂₄H₂₈O₆
Molecular Weight:412.483
Hs Code.:

Synonyms:(1R,3S,4R,5R,6S)-5,6-dibenzyloxy-3-methoxy-4-methoxycarbonylmethyl-2-oxabicyclo<2.2.1>heptane

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Chemical Property of (1R,3S,4R,5R,6S)-5,6-dibenzyloxy-3-methoxy-4-methoxycarbonylmethyl-2-oxabicyclo<2.2.1>heptane

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Technology Process of (1R,3S,4R,5R,6S)-5,6-dibenzyloxy-3-methoxy-4-methoxycarbonylmethyl-2-oxabicyclo<2.2.1>heptane

There total 4 articles about (1R,3S,4R,5R,6S)-5,6-dibenzyloxy-3-methoxy-4-methoxycarbonylmethyl-2-oxabicyclo<2.2.1>heptane 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: 44.0%

: methyl 3,4-di-O-benzyl-6-bromo-2-methoxycarbonylmethylene-6-deoxy-α-D-arabino-hexopyranoside

: 170953-36-3
(1R,3S,4R,5R,6S)-5,6-dibenzyloxy-3-methoxy-4-methoxycarbonylmethyl-2-oxabicyclo<2.2.1>heptane

: [(2S,4R,5R,6R)-4,5-Bis-benzyloxy-2-methoxy-6-methyl-dihydro-pyran-(3E)-ylidene]-acetic acid methyl ester

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 2.5h; Heating;
DOI:10.1007/BF00702406

Reference yield:

: 57783-73-0
methyl 3,4-di-O-benzyl-α-D-glucopyranoside

: 170953-36-3
(1R,3S,4R,5R,6S)-5,6-dibenzyloxy-3-methoxy-4-methoxycarbonylmethyl-2-oxabicyclo<2.2.1>heptane

Guidance literature:: Multi-step reaction with 4 steps

1: 71.5 percent / Ph₃P, CBr₄ / pyridine / 1.5 h / 20 °C

2: 1) (COCl)2, DMSO, 2) Et₃N, HCl / 1) CH₂Cl₂, -60 deg C, 30 min, 2) H₂O, -60 deg C -> 20 deg C

3: 576 mg / tetrahydrofuran / 1.5 h / Heating

4: 44 percent / AIBN, Bu₃SnH / benzene / 2.5 h / Heating

With hydrogenchloride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; tri-n-butyl-tin hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; pyridine; benzene;
DOI:10.1007/BF00702406

Reference yield:

: (2S,4S,5S,6S)-4,5-Bis-benzyloxy-6-bromomethyl-2-methoxy-dihydro-pyran-3-one

: 170953-36-3
(1R,3S,4R,5R,6S)-5,6-dibenzyloxy-3-methoxy-4-methoxycarbonylmethyl-2-oxabicyclo<2.2.1>heptane

Guidance literature:: Multi-step reaction with 2 steps

1: 576 mg / tetrahydrofuran / 1.5 h / Heating

2: 44 percent / AIBN, Bu₃SnH / benzene / 2.5 h / Heating

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In tetrahydrofuran; benzene;
DOI:10.1007/BF00702406