(1S,2S,3S,4S,1'R,3'R,5'R,7'R)-2,3-epoxy-7'-benzyloxymethyl-3',4-dimethylspiro[cyclohexane-1,2'-[8,9]dioxatricyclo[3.3.1.0^3,7]nonan]-4-ol

Base Information

• Chemical Name: (1S,2S,3S,4S,1'R,3'R,5'R,7'R)-2,3-epoxy-7'-benzyloxymethyl-3',4-dimethylspiro[cyclohexane-1,2'-[8,9]dioxatricyclo[3.3.1.0^3,7]nonan]-4-ol
• CAS No.: 656260-04-7
• Molecular Formula: C₂₂H₂₈O₅
• Molecular Weight: 372.461
• Mol file: 656260-04-7.mol

Synonyms:(1S,2S,3S,4S,1'R,3'R,5'R,7'R)-2,3-epoxy-7'-benzyloxymethyl-3',4-dimethylspiro[cyclohexane-1,2'-[8,9]dioxatricyclo[3.3.1.0^3,7]nonan]-4-ol

Chemical Property of (1S,2S,3S,4S,1'R,3'R,5'R,7'R)-2,3-epoxy-7'-benzyloxymethyl-3',4-dimethylspiro[cyclohexane-1,2'-[8,9]dioxatricyclo[3.3.1.0^3,7]nonan]-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3S,4S,1'R,3'R,5'R,7'R)-2,3-epoxy-7'-benzyloxymethyl-3',4-dimethylspiro[cyclohexane-1,2'-[8,9]dioxatricyclo[3.3.1.0^3,7]nonan]-4-ol

There total 2 articles about (1S,2S,3S,4S,1'R,3'R,5'R,7'R)-2,3-epoxy-7'-benzyloxymethyl-3',4-dimethylspiro[cyclohexane-1,2'-[8,9]dioxatricyclo[3.3.1.0^3,7]nonan]-4-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: 66.0%

benzyl bromide (100-39-0) + (1S,2S,3S,4S,1'R,3'R,5'R,7'R)-2,3-epoxy-7'-hydroxymethyl-3',4-dimethylspiro[cyclohexane-1,2'-[8,9]dioxatricyclo[3.3.1.03,7]nonan]-4-ol (594840-06-9) → (1S,2S,3S,4S,1'R,3'R,5'R,7'R)-2,3-epoxy-7'-benzyloxymethyl-3',4-dimethylspiro[cyclohexane-1,2'-[8,9]dioxatricyclo[3.3.1.03,7]nonan]-4-ol (656260-04-7)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 ℃; for 5h;

DOI:10.1021/jo035137x

Reference yield:

(1R,4S,1'R,3'R,5'R,7'R)-7'-hydroxymethyl-3',4-dimethylspiro[cyclohex-2-ene-1,2'-[8,9]-dioxatricyclo[3.3.1.03,7]nonan]-4-ol → (1S,2S,3S,4S,1'R,3'R,5'R,7'R)-2,3-epoxy-7'-benzyloxymethyl-3',4-dimethylspiro[cyclohexane-1,2'-[8,9]dioxatricyclo[3.3.1.03,7]nonan]-4-ol (656260-04-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / Oxone; phosphate buffer / various solvents / 6 h / 0 °C

2: 66 percent / sodium hydride / tetrahydrofuran / 5 h / 0 °C

With Oxone; phosphate buffer; sodium hydride; In tetrahydrofuran; various solvents;

DOI:10.1021/jo035137x

Reference yield: 37.0%

(1S,2S,3S,4S,1'R,3'R,5'R,7'R)-2,3-epoxy-7'-benzyloxymethyl-3',4-dimethylspiro[cyclohexane-1,2'-[8,9]dioxatricyclo[3.3.1.03,7]nonan]-4-ol (656260-04-7) → (1R,3S,5R,7R,9R,10S,13S,14S)-5-benzyloxymethyl-9,13-dimethyl-2,4-dioxatetracyclo[8.3.1.03,10.05.9]tetradecane-7,13,14-triol (656260-05-8)

Guidance literature:

With hydrogenchloride; In methanol;

DOI:10.1021/jo035137x

upstream raw materials:

benzyl bromide

(1S,2S,3S,4S,1'R,3'R,5'R,7'R)-2,3-epoxy-7'-hydroxymethyl-3',4-dimethylspiro[cyclohexane-1,2'-[8,9]dioxatricyclo[3.3.1.0^3,7]nonan]-4-ol

Downstream raw materials:

(1R,3S,5R,7R,9R,10S,13S,14S)-5-benzyloxymethyl-9,13-dimethyl-2,4-dioxatetracyclo[8.3.1.0^3,10.0^5.9]tetradecane-7,13,14-triol