1,2-Cyclopropanedimethanol, 1-acetate, (1R,2S)-

Base Information

• Chemical Name: 1,2-Cyclopropanedimethanol, 1-acetate, (1R,2S)-
• CAS No.: 123809-77-8
• Molecular Formula: C7H12O3
• Molecular Weight: 144.17
• DSSTox Substance ID: DTXSID101242434
• Nikkaji Number: J1.185.204A
• Mol file: 123809-77-8.mol

Synonyms:DTXSID101242434;123809-77-8;1,2-Cyclopropanedimethanol, 1-acetate, (1R,2S)-

Chemical Property of 1,2-Cyclopropanedimethanol, 1-acetate, (1R,2S)-

Chemical Property:

• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 144.078644241
• Heavy Atom Count: 10
• Complexity: 133

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OCC1CC1CO
• Isomeric SMILES: CC(=O)OC[C@H]1C[C@H]1CO

Technology Process of 1,2-Cyclopropanedimethanol, 1-acetate, (1R,2S)-

There total 2 articles about 1,2-Cyclopropanedimethanol, 1-acetate, (1R,2S)- 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:

dimethyl cis-cyclopropane-1,2-dicarboxylate (826-34-6) → Acetic acid (1R,2S)-2-hydroxymethyl-cyclopropylmethyl ester (98516-04-2,118014-41-8,123809-77-8)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAlH₄

2: DMAP / CH₂Cl₂

With dmap; lithium aluminium tetrahydride; In dichloromethane;

DOI:10.1021/jo016161i

Reference yield:

Acetic acid (1R,2S)-2-hydroxymethyl-cyclopropylmethyl ester (98516-04-2,118014-41-8,123809-77-8) → (1R,2S)-1-acetoxymethyl-2-hydroxymethylcyclopropane (98516-04-2) + (1S,2R)-2-(hydroxymethyl)cyclopropane-1-methyl acetate (123809-77-8) + (1R,2S)-2-acetoxymethyl-1-formylcyclopropane (166762-22-7,397274-64-5) + (1S,2R)-2-acetoxymethyl-1-formylcyclopropane (397274-64-5)

Guidance literature:

With tert.-butylhydroperoxide; sodium citrate buffer; chloroperoxidase; polyethylenimine; at 20 ℃; for 1h; pH=5.5; Title compound not separated from byproducts.;

DOI:10.1021/jo016161i

Reference yield: 93.0%

(1S,2R)-2-(hydroxymethyl)cyclopropane-1-methyl acetate (123809-77-8) + p-toluenesulfonyl chloride (98-59-9) → (2R,3S)-4-acetoxy-2,3-methylenebutyl tosylate (400051-47-0)

Guidance literature:

In pyridine; dichloromethane; at 4 ℃; for 12h;

DOI:10.1002/1099-0690(200110)2001:20<3797::AID-EJOC3797>3.0.CO;2-Y

upstream raw materials:

Acetic acid (1R,2S)-2-hydroxymethyl-cyclopropylmethyl ester

dimethyl cis-cyclopropane-1,2-dicarboxylate

Downstream raw materials:

(1R,2S)-2-acetoxymethyl-1-formylcyclopropane

(2R,3S)-4-acetoxy-2,3-methylenebutyl tosylate

(6S,7R)-6,7-methyleneheptadecyl tosylate

(6S,7R)-1-(tert-butyldiphenylsilyloxy)-6,7-methylene-4-heptadecene