(1R,2R,3S,4R)-3,4-di-O-benzyl-5-(benzyloxymethyl)-1,2-O-cyclohexylidenecyclohex-5-ene-1,2,3,4-tetraol

Base Information

Chemical Name:(1R,2R,3S,4R)-3,4-di-O-benzyl-5-(benzyloxymethyl)-1,2-O-cyclohexylidenecyclohex-5-ene-1,2,3,4-tetraol
CAS No.:221371-23-9
Molecular Formula:C₃₄H₃₈O₅
Molecular Weight:526.673
Hs Code.:

Synonyms:(1R,2R,3S,4R)-3,4-di-O-benzyl-5-(benzyloxymethyl)-1,2-O-cyclohexylidenecyclohex-5-ene-1,2,3,4-tetraol

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Chemical Property of (1R,2R,3S,4R)-3,4-di-O-benzyl-5-(benzyloxymethyl)-1,2-O-cyclohexylidenecyclohex-5-ene-1,2,3,4-tetraol

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Technology Process of (1R,2R,3S,4R)-3,4-di-O-benzyl-5-(benzyloxymethyl)-1,2-O-cyclohexylidenecyclohex-5-ene-1,2,3,4-tetraol

There total 3 articles about (1R,2R,3S,4R)-3,4-di-O-benzyl-5-(benzyloxymethyl)-1,2-O-cyclohexylidenecyclohex-5-ene-1,2,3,4-tetraol 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: 70.0%

: 221371-19-3
(1R,2R,3R,4S,5S)-3,4-di-O-benzyl-5-(benzyloxymethyl)-1,2-O-cyclohexylidene-1,2,3,4,5-cyclohexanepentol

: 221371-23-9
(1R,2R,3S,4R)-3,4-di-O-benzyl-5-(benzyloxymethyl)-1,2-O-cyclohexylidenecyclohex-5-ene-1,2,3,4-tetraol

: 221371-22-8
C₆₈H₇₈O₁₃S

Guidance literature:: With pyridine; thionyl chloride; In dichloromethane; at 0 ℃; for 5.5h;
DOI:10.1021/jo982024i

Reference yield:

: 100-39-0
benzyl bromide

: 221371-23-9
(1R,2R,3S,4R)-3,4-di-O-benzyl-5-(benzyloxymethyl)-1,2-O-cyclohexylidenecyclohex-5-ene-1,2,3,4-tetraol

Guidance literature:: Multi-step reaction with 2 steps

1: 85 percent / NaH, Bu₄NI / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) room temp., overnight

2: 70 percent / SOCl₂, pyridine / CH₂Cl₂ / 5.5 h / 0 °C

With pyridine; thionyl chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo982024i

Reference yield:

: 183268-55-5
(1R,2R,3S,4S,5S)-3-O-benzyl-5-((benzyloxy)methyl)-1,2-O-cyclohexylidenecyclohexane-1,2,3,4,5-pentol

: 221371-23-9
(1R,2R,3S,4R)-3,4-di-O-benzyl-5-(benzyloxymethyl)-1,2-O-cyclohexylidenecyclohex-5-ene-1,2,3,4-tetraol

Guidance literature:: Multi-step reaction with 2 steps

1: 85 percent / NaH, Bu₄NI / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) room temp., overnight

2: 70 percent / SOCl₂, pyridine / CH₂Cl₂ / 5.5 h / 0 °C

With pyridine; thionyl chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo982024i