(1R,2R,3S,5R)-3-(benzyloxy)-pinanediol

Base Information

• Chemical Name: (1R,2R,3S,5R)-3-(benzyloxy)-pinanediol
• CAS No.: 318993-93-0
• Molecular Formula: C₁₇H₂₄O₂
• Molecular Weight: 260.376
• Mol file: 318993-93-0.mol

Synonyms:(1R,2R,3S,5R)-3-(benzyloxy)-pinanediol

Chemical Property of (1R,2R,3S,5R)-3-(benzyloxy)-pinanediol

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of (1R,2R,3S,5R)-3-(benzyloxy)-pinanediol

There total 3 articles about (1R,2R,3S,5R)-3-(benzyloxy)-pinanediol 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: 78.0%

(1R,2R,3S,5R)-2,3-pinane diol (22422-34-0) + benzyl bromide (100-39-0) → (1R,2R,3S,5R)-3-(benzyloxy)-pinanediol (318993-93-0)

Guidance literature:

With potassium carbonate; potassium iodide; 2-aminoethoxydiphenyl borate; In acetonitrile; at 60 ℃; for 24h;

DOI:10.1021/jacs.1c00759

Reference yield: 11.0%

(1R,2R,3S,5R)-2,3-pinane diol (22422-34-0) + benzyl bromide (100-39-0) → (1R,2R,3S,5R)-2-(benzyloxy)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ol (1338323-34-4) + (1R,2R,3S,5R)-3-(benzyloxy)-pinanediol (318993-93-0)

Guidance literature:

With 2-Aminoethoxydiphenylborane; potassium carbonate; potassium iodide; In acetonitrile; at 60 ℃; for 24h; regioselective reaction; Inert atmosphere;

DOI:10.1021/ja302549c

Reference yield:

(1R,2R,3S,5R)-2,3-pinane diol (22422-34-0) + benzyl chloride (100-44-7) → (1R,2R,3S,5R)-3-(benzyloxy)-pinanediol (318993-93-0)

Guidance literature:

(1R,2R,3S,5R)-2,3-pinane diol; With sodium hydride; In dimethyl sulfoxide; at 20 ℃; for 10h;

benzyl chloride; In dimethyl sulfoxide; for 1h;

DOI:10.1016/S0957-4166(00)00301-3

upstream raw materials:

(1R,2R,3S,5R)-2,3-pinane diol

benzyl chloride

benzyl bromide

Downstream raw materials:

(1R,2R,3S,5R)-3-O-benzylpinanediol propionate

Refernces

• 1、 Lee, Doris,Williamson, Caitlin L.,Chan, Lina,Taylor, Mark S.. "Regioselective, borinic acid-catalyzed monoacylation, sulfonylation and alkylation of diols and carbohydrates: Expansion of substrate scope and mechanistic studies". supporting information; experimental part. p. 8260 - 8267. Retrieved 2012/07/14.