<1R-(1α,2α,3β,4α,5β)>-3-Methyl-4,5-bis(phenylmethoxy)-2-<(phenylmethoxy)methyl>cyclopentanol

Base Information

• Chemical Name: <1R-(1α,2α,3β,4α,5β)>-3-Methyl-4,5-bis(phenylmethoxy)-2-<(phenylmethoxy)methyl>cyclopentanol
• CAS No.: 106139-79-1
• Molecular Formula: C₂₈H₃₂O₄
• Molecular Weight: 432.56
• Mol file: 106139-79-1.mol

Synonyms:<1R-(1α,2α,3β,4α,5β)>-3-Methyl-4,5-bis(phenylmethoxy)-2-<(phenylmethoxy)methyl>cyclopentanol

Chemical Property of <1R-(1α,2α,3β,4α,5β)>-3-Methyl-4,5-bis(phenylmethoxy)-2-<(phenylmethoxy)methyl>cyclopentanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <1R-(1α,2α,3β,4α,5β)>-3-Methyl-4,5-bis(phenylmethoxy)-2-<(phenylmethoxy)methyl>cyclopentanol

There total 4 articles about <1R-(1α,2α,3β,4α,5β)>-3-Methyl-4,5-bis(phenylmethoxy)-2-<(phenylmethoxy)methyl>cyclopentanol 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: 4.5%

<(2R)-(2α,4aβ,5β,6α,7β,7aβ)>-Hexahydro-5-methyl-2-phenyl-6,7-bis(phenylmethoxy)cyclopenta-1,3-dioxin (106139-72-4) → <1S-(1α,2β,3α,4β,5α)>-2-Methyl-3,4,5-tris(phenylmethoxy)cyclopentanemethanol (106139-78-0) + <1R-(1α,2α,3β,4α,5β)>-3-Methyl-4,5-bis(phenylmethoxy)-2-<(phenylmethoxy)methyl>cyclopentanol (106139-79-1)

Guidance literature:

With lithium aluminium tetrahydride; aluminium trichloride; In diethyl ether; dichloromethane; for 0.666667h;

DOI:10.1021/ja00187a031

Reference yield:

(R)-1,2-Dideoxy-3,4-bis-O-(phenylmethyl)-5,7-O-(phenylmethylene)-D-gluco-hept-1-enitol (119111-07-8) → <1R-(1α,2α,3β,4α,5β)>-3-Methyl-4,5-bis(phenylmethoxy)-2-<(phenylmethoxy)methyl>cyclopentanol (106139-79-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / CH₂Cl₂ / 2 h / Heating

2: 57 percent / AIBN, Bu₃SnH / toluene / 3 h / Heating

3: 44 percent / LAH, AlCl₃ / CH₂Cl₂; diethyl ether / 0.67 h

With lithium aluminium tetrahydride; aluminium trichloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In diethyl ether; dichloromethane; toluene;

DOI:10.1021/ja00187a031

Reference yield:

2,3-di-O-benzyl-4,6-O-benzylidene-D-glucopyranose (20770-84-7,113566-69-1,113566-70-4) → <1R-(1α,2α,3β,4α,5β)>-3-Methyl-4,5-bis(phenylmethoxy)-2-<(phenylmethoxy)methyl>cyclopentanol (106139-79-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) n-BuLi / 1.) THF, hexane, -20 deg C --> room temp., 1h, 2.) -20 deg C --> room temp., 16h, 3.) 50 deg C, 15 min

2: 68 percent / CH₂Cl₂ / 2 h / Heating

3: 57 percent / AIBN, Bu₃SnH / toluene / 3 h / Heating

4: 44 percent / LAH, AlCl₃ / CH₂Cl₂; diethyl ether / 0.67 h

With lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In diethyl ether; dichloromethane; toluene;

DOI:10.1021/ja00187a031

upstream raw materials:

<(2R)-(2α,4aβ,5β,6α,7β,7aβ)>-Hexahydro-5-methyl-2-phenyl-6,7-bis(phenylmethoxy)cyclopenta-1,3-dioxin

(R)-1,2-Dideoxy-3,4-bis-O-(phenylmethyl)-5,7-O-(phenylmethylene)-D-gluco-hept-1-enitol

2,3-di-O-benzyl-4,6-O-benzylidene-D-glucopyranose

Imidazole-1-carbothioic acid O-[(2R,4R,5R)-4-((1R,2S)-1,2-bis-benzyloxy-but-3-enyl)-2-phenyl-[1,3]dioxan-5-yl] ester

Downstream raw materials:

C₃₅H₃₈O₄