(1S,2S)-3,3-dimethoxy-1,2-cyclobutanedimethanol

Base Information

• Chemical Name: (1S,2S)-3,3-dimethoxy-1,2-cyclobutanedimethanol
• CAS No.: 138736-92-2
• Molecular Formula: C8H16O4
• Molecular Weight: 176.213
• DSSTox Substance ID: DTXSID401242221
• Nikkaji Number: J2.270.668C
• Mol file: 138736-92-2.mol

Synonyms:138736-92-2;(1S,2S)-3,3-dimethoxy-1,2-cyclobutanedimethanol;[(1S,2S)-2-(hydroxymethyl)-3,3-dimethoxycyclobutyl]methanol;((1S,2S)-3,3-Dimethoxycyclobutane-1,2-diyl)dimethanol;starbld0006661;SCHEMBL9025968;GFOWJYFIBONBSM-RNFRBKRXSA-N;DTXSID401242221;AKOS030241069;J-500436;(1S,2S)-3,3-Dimethoxycyclobutane-1alpha,2beta-dimethanol

Chemical Property of (1S,2S)-3,3-dimethoxy-1,2-cyclobutanedimethanol

Chemical Property:

• Boiling Point: 265.6±10.0 °C(Predicted)
• PKA: 15.05±0.10(Predicted)
• PSA: 58.92000
• Density: 1.16±0.1 g/cm3(Predicted)
• LogP: -0.40380
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 176.10485899
• Heavy Atom Count: 12
• Complexity: 144

Purity/Quality:

(1S,2S)-3,3-Dimethoxy-1,2-cyclobutanedimethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1(CC(C1CO)CO)OC
• Isomeric SMILES: COC1(C[C@@H]([C@H]1CO)CO)OC
• Uses: Intermediate in the preparation of dideoxy nucleoside derivatives.

Technology Process of (1S,2S)-3,3-dimethoxy-1,2-cyclobutanedimethanol

There total 1 articles about (1S,2S)-3,3-dimethoxy-1,2-cyclobutanedimethanol 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%

(1S,2R)-3,3-Dimethoxy-cyclobutane-1,2-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester (138736-91-1) → (2S,3R)-(+)-bis[hydroxymethyl]-1,1-dimethoxycyclobutane (138736-92-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran;

DOI:10.1016/0040-4039(91)85023-X

Reference yield: 100.0%

(2S,3R)-(+)-bis[hydroxymethyl]-1,1-dimethoxycyclobutane (138736-92-2) + tert-butylchlorodiphenylsilane (58479-61-1) → C40H52O4Si2

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 16h;

Reference yield: 87.0%

benzoyl chloride (98-88-4) + (2S,3R)-(+)-bis[hydroxymethyl]-1,1-dimethoxycyclobutane (138736-92-2) → C22H24O6 (138736-93-3)

Guidance literature:

With pyridine; Inert atmosphere;

DOI:10.1021/acs.joc.1c00784

upstream raw materials:

(1S,2R)-3,3-Dimethoxy-cyclobutane-1,2-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester

Downstream raw materials:

C₂₂H₂₄O₆

(2S-trans)-2,3-bis[(benzoyloxy)methyl]cyclobutanone

3(S)-trans-3,4-Bis<(benzoyloxy)methyl>cyclopentanone

3(S)-trans-3,4-Bis<(benzoyloxy)methyl>cyclopentanone oxime