(1S,2S)-1,2-Bis(MethanesulfonyloxyMethyl)cyclohexane

Base Information

• Chemical Name: (1S,2S)-1,2-Bis(MethanesulfonyloxyMethyl)cyclohexane
• CAS No.: 173658-50-9
• Molecular Formula: C10H20O6S2
• Molecular Weight: 300.397
• Mol file: 173658-50-9.mol

Synonyms:(1S,2S)-1,2-BIS(METHANESULFONYLOXYMETHYL)CYCLOHEXANE;

Chemical Property of (1S,2S)-1,2-Bis(MethanesulfonyloxyMethyl)cyclohexane

Chemical Property:

• PSA: 103.50000
• Density: 1.270±0.06 g/cm3 (20 oC 760 Torr)
• LogP: 2.90680

Purity/Quality:

98%Min ^*data from raw suppliers

(1S,2S)-Cyclohexane-1,2-diylbis(methylene)dimethanesulfonate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (1S,2S)-1,2-Bis(methanesulfonyloxymethyl)cyclohexane is used as a reactant in the preparation of lurasidone, a schizophrenia drug.

Technology Process of (1S,2S)-1,2-Bis(MethanesulfonyloxyMethyl)cyclohexane

There total 4 articles about (1S,2S)-1,2-Bis(MethanesulfonyloxyMethyl)cyclohexane 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: 90.0%

(1S,2S)-(–)-1,2-di(hydroxymethyl)cyclohexane (3205-34-3,25712-33-8) + methanesulfonyl chloride (124-63-0) → (1S,2S)-cyclohexane-1,2-dimethanol bis(methanesulfonate) (173658-50-9)

Guidance literature:

With triethylamine; In diethyl ether; 1) 0 deg C, 20 min; 2) rt, 2 h;

DOI:10.1021/jo951647i

Reference yield:

(1S,2S)-cyclohexane-1,2-dicarboxylic acid (610-10-6,1687-30-5,2305-32-0,21963-41-7,46022-05-3,610-09-3) → (1S,2S)-cyclohexane-1,2-dimethanol bis(methanesulfonate) (173658-50-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / LiAlH₄ / diethyl ether / 20 h / 36 °C

2: 69 percent / pyridine / 12 h / 25 °C

With pyridine; lithium aluminium tetrahydride; In diethyl ether;

DOI:10.1016/S0957-4166(97)00052-9

Reference yield:

(4S,5S)-4,5-bis(hydroxymethyl)cyclohexene (15679-27-3) → (1S,2S)-cyclohexane-1,2-dimethanol bis(methanesulfonate) (173658-50-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / H₂ / Pd/C / ethanol / 1.5 h / 1654.9 Torr

2: 90 percent / Et₃N / diethyl ether / 1) 0 deg C, 20 min; 2) rt, 2 h

With hydrogen; triethylamine; palladium on activated charcoal; In diethyl ether; ethanol;

DOI:10.1021/jo951647i

upstream raw materials:

(1S,2S)-(–)-1,2-di(hydroxymethyl)cyclohexane

methanesulfonyl chloride

(1S,2S)-cyclohexane-1,2-dicarboxylic acid

trans-1,2-cyclohexanedicarboxylic acid

Downstream raw materials:

lurasidone

(3aR,4S,7R,7aS)-2-[((1R,2R)-2-{[4-(l1,2-benzisothiazol-3-yl)piperazin-1-yl]methyl}cyclohexyl)methyl]hexahydro-1H-4,7-methanisoindol-1,3-dione hydrochloride

(1S,2S)-1,2-Bis-iodomethyl-cyclohexane

(1R,2R)-cyclohexane-1,2-diacetonitrile

Refernces

• 1、 Longeau, Alexia,Durand, Sandrine,Spiegel, Anja,Knoechel, Paul. "Synthesis of new C2-symmetrical diphosphines using chiral zinc organometallics". . p. 987 - 990. Retrieved 2007/10/03.