[(4s,5s)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl]dimethanediyl dimethanesulfonate

Base Information

• Chemical Name: [(4s,5s)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl]dimethanediyl dimethanesulfonate
• CAS No.: 4248-74-2
• Molecular Formula: C9H18 O8 S2
• Molecular Weight: 318.369
• Hs Code.: 2932999099
• European Community (EC) Number: 610-032-2
• NSC Number: 60499
• DSSTox Substance ID: DTXSID30289366
• Wikidata: Q82026635
• Mol file: 4248-74-2.mol

Synonyms:4248-74-2;[(4s,5s)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]dimethanediyl dimethanesulfonate;[(4S,5S)-2,2-dimethyl-5-(methylsulfonyloxymethyl)-1,3-dioxolan-4-yl]methyl methanesulfonate;(-)-2,3-O-Isopropylidene-L-threitol-1,4-dimethane sulfonate;(-)-2,3-O-ISOPROPYLIDENE-L-THREITOL 1,4-DIMETHANE SULFONATE;NSC60499;1,3-Dioxolane-4,5-dimethanol,2,2-dimethyl-, 4,5-dimethanesulfonate, (4S,5S)-;SCHEMBL8529382;DTXSID30289366;NSC 60499;NSC-60499;CS-0097525

Chemical Property of [(4s,5s)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl]dimethanediyl dimethanesulfonate

Chemical Property:

• Vapor Pressure: 1.11E-09mmHg at 25°C
• Refractive Index: 1.466
• Boiling Point: 501.1°Cat760mmHg
• Flash Point: 256.9°C
• PSA: 121.96000
• Density: 1.331g/cm³
• LogP: 1.62050
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 318.04430988
• Heavy Atom Count: 19
• Complexity: 449

Purity/Quality:

99% ^*data from raw suppliers

(-)-2,3-O-Isopropylidene-L-threitol-1,4-dimethane sulfonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC(C(O1)COS(=O)(=O)C)COS(=O)(=O)C)C
• Isomeric SMILES: CC1(O[C@H]([C@@H](O1)COS(=O)(=O)C)COS(=O)(=O)C)C

Technology Process of [(4s,5s)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl]dimethanediyl dimethanesulfonate

There total 6 articles about [(4s,5s)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl]dimethanediyl dimethanesulfonate 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: 98.0%

2,3-O-isopropylidene-L-threitol (50622-09-8) + methanesulfonyl chloride (124-63-0) → ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene) dimethanesulfonate (4248-74-2)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1021/acs.orglett.6b03554

Reference yield:

dimethyl 2,2-dimethyl-1,3-dioxolane-trans-4,5-dicarboxylate (116499-08-2) → 2,3-O-Isopropyliden-DL-threitol-1,4-bis-methansulfonat (4248-74-2,38279-61-7,94943-42-7,109281-59-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate

2: triethylamine / dichloromethane

With sodium tetrahydroborate; triethylamine; In dichloromethane;

DOI:10.1039/c9sc05997k

Reference yield:

2,3-O-Isopropyliden-DL-threitol (25432-12-6,50622-09-8,55904-12-6,69460-89-5,73346-74-4,86992-57-6) + methanesulfonyl chloride (124-63-0) → 2,3-O-Isopropyliden-DL-threitol-1,4-bis-methansulfonat (4248-74-2,38279-61-7,94943-42-7,109281-59-6)

Guidance literature:

With triethylamine; In dichloromethane;

DOI:10.1039/c9sc05997k

upstream raw materials:

2,3-O-isopropylidene-L-threitol

methanesulfonyl chloride

(-)-dimethy-2,3-O-isopropylidene-L-tartrate

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

Downstream raw materials:

DL-Threitol-1,4-bis-methansulfonat

(-)-2,2-dimethyl-4,5-bis(phenylsulfanylmethyl)-1,3-dioxolane

((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)dimethanamine

(-)-Diop

Refernces

• 1、 Fang, Jianguo,Hou, Yanan,Li, Jin,Li, Xinming,Wang, Song,Zhao, Jintao. "Combination of chemotherapy and oxidative stress to enhance cancer cell apoptosis". . p. 3215 - 3222. Retrieved 2020/04/08.
• 2、 Diehl (née Knobloch), Eva,Brückner, Reinhard. "Turning the Nitrogen Atoms of an Ar2P?CH2?N?N?CH2?PAr2 Motif into Uniquely Configured Stereocenters: A Novel Diphosphane Design for Asymmetric Catalysis". supporting information. p. 3429 - 3433. Retrieved 2018/02/16.