(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

Base Information

• Chemical Name: (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
• CAS No.: 656260-05-8
• Molecular Formula: C₂₂H₃₀O₆
• Molecular Weight: 390.477

Synonyms:(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

Chemical Property of (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

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Technology Process of (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

There total 4 articles about (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 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: 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

Reference yield:

benzyl bromide (100-39-0) → (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:

Multi-step reaction with 2 steps

1: 66 percent / sodium hydride / tetrahydrofuran / 5 h / 0 °C

2: 37 percent / hydrogen chloride / methanol

With hydrogenchloride; sodium hydride; In tetrahydrofuran; methanol;

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 → (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:

Multi-step reaction with 3 steps

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

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

3: 37 percent / hydrogen chloride / methanol

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

DOI:10.1021/jo035137x

upstream raw materials:

(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

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

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