(1R,2S,5S)-1-{[bis(4-methoxyphenyl)phenylmethoxy]methyl}bicyclo[3.1.0]hexan-2-ol

Base Information

• Chemical Name: (1R,2S,5S)-1-{[bis(4-methoxyphenyl)phenylmethoxy]methyl}bicyclo[3.1.0]hexan-2-ol
• CAS No.: 325464-44-6
• Molecular Formula: C₂₈H₃₀O₄
• Molecular Weight: 430.544
• Mol file: 325464-44-6.mol

Synonyms:(1R,2S,5S)-1-{[bis(4-methoxyphenyl)phenylmethoxy]methyl}bicyclo[3.1.0]hexan-2-ol

Chemical Property of (1R,2S,5S)-1-{[bis(4-methoxyphenyl)phenylmethoxy]methyl}bicyclo[3.1.0]hexan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,5S)-1-{[bis(4-methoxyphenyl)phenylmethoxy]methyl}bicyclo[3.1.0]hexan-2-ol

There total 8 articles about (1R,2S,5S)-1-{[bis(4-methoxyphenyl)phenylmethoxy]methyl}bicyclo[3.1.0]hexan-2-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: 60.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + (1R,2S,5S)-1-(hydroxymethyl)bicyclo[3.1.0]hexan-2-ol (325464-43-5) → (1R,2S,5S)-1-{[bis(4-methoxyphenyl)phenylmethoxy]methyl}bicyclo[3.1.0]hexan-2-ol (325464-44-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;

DOI:10.1081/NCN-100002319

Reference yield:

((1S,2R)-2-Benzyloxymethyl-cyclopent-3-enyloxy)-tert-butyl-diphenyl-silane (191480-67-8) → (1R,2S,5S)-1-{[bis(4-methoxyphenyl)phenylmethoxy]methyl}bicyclo[3.1.0]hexan-2-ol (325464-44-6)

Guidance literature:

Multi-step reaction with 9 steps

1: dimethylsulfoxide

2: 73 percent / NaIO₄ / methanol; H₂O

3: SO₃; pyridine

4: LiAlH₄ / tetrahydrofuran

5: 99 percent / TBAF / acetonitrile

6: 88 percent / Et₂Zn / CH₂Cl₂

7: HCO₂H / Pd / methanol

8: 60 percent / DBU / CH₂Cl₂

With pyridine; sodium periodate; lithium aluminium tetrahydride; formic acid; sulfur trioxide; tetrabutyl ammonium fluoride; diethylzinc; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile;

DOI:10.1081/NCN-100002319

Reference yield:

(1S)-2-[(phenylmethoxy)methyl]cyclopent-2-en-1-ol (325464-40-2) → (1R,2S,5S)-1-{[bis(4-methoxyphenyl)phenylmethoxy]methyl}bicyclo[3.1.0]hexan-2-ol (325464-44-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / Et₂Zn / CH₂Cl₂

2: HCO₂H / Pd / methanol

3: 60 percent / DBU / CH₂Cl₂

With formic acid; diethylzinc; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium; In methanol; dichloromethane;

DOI:10.1081/NCN-100002319

upstream raw materials:

4,4'-dimethoxytrityl chloride

(1R,2S,5S)-1-(hydroxymethyl)bicyclo[3.1.0]hexan-2-ol

((1S,2R)-2-Benzyloxymethyl-cyclopent-3-enyloxy)-tert-butyl-diphenyl-silane

(1S)-2-[(phenylmethoxy)methyl]cyclopent-2-en-1-ol