(1R,4R,5S,6S)-4,5,6-tris(phenylmethoxy)cyclohex-2-en-1-ol

Base Information

• Chemical Name: (1R,4R,5S,6S)-4,5,6-tris(phenylmethoxy)cyclohex-2-en-1-ol
• CAS No.: 220564-16-9
• Molecular Formula: C27H28O4
• Molecular Weight: 416.517
• DSSTox Substance ID: DTXSID20448627
• Nikkaji Number: J1.643.046C
• Wikidata: Q82267709
• Mol file: 220564-16-9.mol

Synonyms:CTK0I8871;220564-16-9;DTXSID20448627;(1R)-4beta,5alpha,6beta-Tris(benzyloxy)-2-cyclohexene-1alpha-ol

Chemical Property of (1R,4R,5S,6S)-4,5,6-tris(phenylmethoxy)cyclohex-2-en-1-ol

Chemical Property:

• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 416.19875937
• Heavy Atom Count: 31
• Complexity: 517

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC2C=CC(C(C2OCC3=CC=CC=C3)OCC4=CC=CC=C4)O
• Isomeric SMILES: C1=CC=C(C=C1)CO[C@@H]2C=C[C@H]([C@@H]([C@H]2OCC3=CC=CC=C3)OCC4=CC=CC=C4)O

Technology Process of (1R,4R,5S,6S)-4,5,6-tris(phenylmethoxy)cyclohex-2-en-1-ol

There total 23 articles about (1R,4R,5S,6S)-4,5,6-tris(phenylmethoxy)cyclohex-2-en-1-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: 90.0%

(-)-(1R,2R,3S,4R)-1-pivaloxy-2,3,4-tribenzyloxy-5-cyclohexene (382601-71-0) → (-)-(1R,2S,3S,4R)-2,3,4-tribenzyloxy-5-cyclohexene-1-ol (220564-16-9)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃;

DOI:10.1016/S0040-4039(98)02274-6

Reference yield: 69.0%

(4S,5S,6R)-4,5,6-tris(benzyloxy)octa-1,7-dien-3-ol → (-)-(1R,2S,3S,4R)-2,3,4-tribenzyloxy-5-cyclohexene-1-ol (220564-16-9) + (1S,4S,5S,6S)-4,5,6-tris(benzyloxy)cyclohex-2-enol (800408-98-4)

Guidance literature:

(4S,5S,6R)-4,5,6-tris(benzyloxy)octa-1,7-dien-3-ol; Grubbs catalyst first generation; In dichloromethane; at 20 ℃; for 16h;

With tris(hydroxymethyl)phosphine; In dichloromethane; at 20 ℃;

DOI:10.1039/b411021h

Reference yield:

(4R,5S,6R)-4,5,6-tris(benzyloxy)cyclohex-2-en-1-one (671199-46-5) → (-)-(1R,2S,3S,4R)-2,3,4-tribenzyloxy-5-cyclohexene-1-ol (220564-16-9)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at 0 ℃; for 2h;

DOI:10.1039/b411021h

upstream raw materials:

(-)-(1R,2R,3S,4R)-1-pivaloxy-2,3,4-tribenzyloxy-5-cyclohexene

(4R,5S,6R)-4,5,6-tris(benzyloxy)cyclohex-2-en-1-one

(1S,4S,5S,6S)-4,5,6-tris(benzyloxy)cyclohex-2-enol

benzyl bromide

Downstream raw materials:

(1R,2R,5S,6S)-5,6-bis(benzyloxy)-2-{[(tert-butyldimethylsilyl)-oxy]methyl}cyclohex-3-en-1-ol

Phosphoric acid benzyl ester (R)-2-benzyloxy-3-hexadecyloxy-propyl ester (1R,2R,3S,4R)-2,3,4-tris-benzyloxy-cyclohexyl ester

Diisopropyl-phosphoramidous acid benzyl ester (1R,2R,3S,4R)-2,3,4-tris-benzyloxy-cyclohexyl ester

1D-2,3-anhydro-4,5,6-tri-O-benzyl-myo-inositol