(+/-)-(1α,2α,5α,6β)-5,6-Bis(benzyloxy)cyclohex-3-ene-1,2-diol

Base Information

• Chemical Name: (+/-)-(1α,2α,5α,6β)-5,6-Bis(benzyloxy)cyclohex-3-ene-1,2-diol
• CAS No.: 130633-15-7
• Molecular Formula: C₂₀H₂₂O₄
• Molecular Weight: 326.392
• Mol file: 130633-15-7.mol

Synonyms:(+/-)-(1α,2α,5α,6β)-5,6-Bis(benzyloxy)cyclohex-3-ene-1,2-diol

Chemical Property of (+/-)-(1α,2α,5α,6β)-5,6-Bis(benzyloxy)cyclohex-3-ene-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-(1α,2α,5α,6β)-5,6-Bis(benzyloxy)cyclohex-3-ene-1,2-diol

There total 7 articles about (+/-)-(1α,2α,5α,6β)-5,6-Bis(benzyloxy)cyclohex-3-ene-1,2-diol 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: 100.0%

(3aα,6β,7α,7aα)-6,7-bis(benzyloxy)-3a,6,7,7a-tetrahydrobenzo-1,3-dioxol-2-one (118993-50-3,130633-14-6) → (+/-)-(1α,2α,5α,6β)-5,6-Bis(benzyloxy)cyclohex-3-ene-1,2-diol (130633-15-7)

Guidance literature:

With water; triethylamine; In methanol; for 90h; Ambient temperature;

Reference yield:

cis-1,2-dihydrocatechol (17793-95-2) → (+/-)-(1α,2α,5α,6β)-5,6-Bis(benzyloxy)cyclohex-3-ene-1,2-diol (130633-15-7)

Guidance literature:

Multi-step reaction with 5 steps

1: MeONa / methanol / 0.33 h / Ambient temperature

2: m-chloroperbenzoic acid / CH₂Cl₂ / 40 h / Ambient temperature

3: 85 percent / camphersulphonic acid*H₂O / CH₂Cl₂ / 23.5 h / Ambient temperature

4: 81 percent / Ag₂O / dimethylformamide / 39.5 h / Ambient temperature

5: 100 percent / Et₃N, H₂O / methanol / 90 h / Ambient temperature

With camphor-10-sulfonic acid; water; sodium methylate; triethylamine; 3-chloro-benzenecarboperoxoic acid; silver(l) oxide; In methanol; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

(3aS,7aR)-3a,7a-Dihydro-benzo[1,3]dioxol-2-one (118993-48-9) → (+/-)-(1α,2α,5α,6β)-5,6-Bis(benzyloxy)cyclohex-3-ene-1,2-diol (130633-15-7)

Guidance literature:

Multi-step reaction with 4 steps

1: m-chloroperbenzoic acid / CH₂Cl₂ / 40 h / Ambient temperature

2: 85 percent / camphersulphonic acid*H₂O / CH₂Cl₂ / 23.5 h / Ambient temperature

3: 81 percent / Ag₂O / dimethylformamide / 39.5 h / Ambient temperature

4: 100 percent / Et₃N, H₂O / methanol / 90 h / Ambient temperature

With camphor-10-sulfonic acid; water; triethylamine; 3-chloro-benzenecarboperoxoic acid; silver(l) oxide; In methanol; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

(3aα,6β,7α,7aα)-6,7-bis(benzyloxy)-3a,6,7,7a-tetrahydrobenzo-1,3-dioxol-2-one

D-myo-inositol

benzyl bromide

cis-1,2-dihydrocatechol

Downstream raw materials:

(3aα,4α,5β,6β,7β,7aα)-4,5-bis(benzyloxy)-6,7-epoxyhexahydro-2,2-dimethylbenzo-1,3-dioxole

(3aα,4α,5β,6α,7α,7aα)-4,5-bis(benzyloxy)-6,7-epoxyhexahydro-2,2-dimethylbenzo-1,3-dioxole

(1R,2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-7-oxa-bicyclo[4.1.0]heptane-2,3-diol

(1α,2α,3β,4α,5α,6α)-3,4-bis(benzyloxy)-5,6-epoxycyclohexane-1,2-diol