(1R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-[(benzyloxy)methyl]cyclohex-2-enol

Base Information

Chemical Name:(1R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-[(benzyloxy)methyl]cyclohex-2-enol
CAS No.:1307860-08-7
Molecular Formula:C₃₅H₃₆O₅
Molecular Weight:536.668
Hs Code.:

Synonyms:(1R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-[(benzyloxy)methyl]cyclohex-2-enol

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Chemical Property of (1R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-[(benzyloxy)methyl]cyclohex-2-enol

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Technology Process of (1R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-[(benzyloxy)methyl]cyclohex-2-enol

There total 7 articles about (1R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-[(benzyloxy)methyl]cyclohex-2-enol 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: 28.0%

: (3R,4S,5R,6RS)-1,3,4,5-tetra-O-benzyl-1,3,4,5,6-pentahydroxy-2-methylene-oct-7-ene

: 1307860-08-7
(1R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-[(benzyloxy)methyl]cyclohex-2-enol

: 1307860-10-1
(1S,4R,5S,6R)-4,5,6-Tris(benzyloxy)-3-[(benzyloxy)methyl-]cyclohex-2-enol

Guidance literature:: (3R,4S,5R,6RS)-1,3,4,5-tetra-O-benzyl-1,3,4,5,6-pentahydroxy-2-methylene-oct-7-ene; With Hoveyda-Grubbs catalyst second generation; In toluene; at 60 ℃; for 6.75h; Inert atmosphere;

With Hoveyda-Grubbs catalyst second generation; In dimethyl sulfoxide; at 20 ℃; for 16h; Inert atmosphere;
DOI:10.1016/j.tetasy.2011.02.013

Reference yield: 27.0%

: 1307860-04-3
C₃₇H₄₀O₅

: 1307860-08-7
(1R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-[(benzyloxy)methyl]cyclohex-2-enol

: 1307860-10-1
(1S,4R,5S,6R)-4,5,6-Tris(benzyloxy)-3-[(benzyloxy)methyl-]cyclohex-2-enol

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 4h; Reflux;
DOI:10.1002/ejoc.201301782

Reference yield:

: 1605289-88-0
(2R,3S,4R)-5-[(benzyloxy)methyl]hex-5-ene-1,2,3,4-tetraol

: 1307860-08-7
(1R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-[(benzyloxy)methyl]cyclohex-2-enol

Guidance literature:: Multi-step reaction with 6 steps

1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C

3: toluene-4-sulfonic acid / chloroform; methanol / 3 h / 20 °C

4: Dess-Martin periodane / dichloromethane / 2 h / 20 °C

5: tetrahydrofuran / -78 °C

6: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 4 h / Reflux

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; mineral oil;
DOI:10.1002/ejoc.201301782