methanesulfonic acid {(4R)-(2,2-dimethyl[1,3]dioxolan-4-yl)}-{(4S,5S)-(5-methanesulfonyloxymethyl-2,2-dimethyl[1,3]dioxolan-4-yl)}-(S)methyl ester

Base Information

Chemical Name:methanesulfonic acid {(4R)-(2,2-dimethyl[1,3]dioxolan-4-yl)}-{(4S,5S)-(5-methanesulfonyloxymethyl-2,2-dimethyl[1,3]dioxolan-4-yl)}-(S)methyl ester
CAS No.:7115-24-4
Molecular Formula:C14H26O10S2
Molecular Weight:418.486
Hs Code.:
DSSTox Substance ID:DTXSID10452379
Mol file:7115-24-4.mol

methanesulfonic acid {(4R)-(2,2-dimethyl[1,3]dioxolan-4-yl)}-{(4S,5S)-(5-methanesulfonyloxymethyl-2,2-dimethyl[1,3]dioxolan-4-yl)}-(S)methyl ester

Synonyms:7115-24-4;SCHEMBL6102466;DTXSID10452379;GSDSCWGTQKUWGC-RHYQMDGZSA-N;AG-G-78469;methanesulfonic acid {(4R)-(2,2-dimethyl[1,3]dioxolan-4-yl)}-{(4S,5S)-(5-methanesulfonyloxymethyl-2,2-dimethyl[1,3]dioxolan-4-yl)}-(S)methyl ester

Suppliers and Price of methanesulfonic acid {(4R)-(2,2-dimethyl[1,3]dioxolan-4-yl)}-{(4S,5S)-(5-methanesulfonyloxymethyl-2,2-dimethyl[1,3]dioxolan-4-yl)}-(S)methyl ester

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of methanesulfonic acid {(4R)-(2,2-dimethyl[1,3]dioxolan-4-yl)}-{(4S,5S)-(5-methanesulfonyloxymethyl-2,2-dimethyl[1,3]dioxolan-4-yl)}-(S)methyl ester

Chemical Property:

PSA：140.42000
LogP:2.14060
XLogP3:-0.3
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:7
Exact Mass:418.09673937
Heavy Atom Count:26
Complexity:701

Purity/Quality:: 99% ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC1(OCC(O1)C(C2C(OC(O2)(C)C)COS(=O)(=O)C)OS(=O)(=O)C)C
Isomeric SMILES:CC1(OC[C@@H](O1)[C@@H]([C@@H]2[C@@H](OC(O2)(C)C)COS(=O)(=O)C)OS(=O)(=O)C)C

Technology Process of methanesulfonic acid {(4R)-(2,2-dimethyl[1,3]dioxolan-4-yl)}-{(4S,5S)-(5-methanesulfonyloxymethyl-2,2-dimethyl[1,3]dioxolan-4-yl)}-(S)methyl ester

There total 12 articles about methanesulfonic acid {(4R)-(2,2-dimethyl[1,3]dioxolan-4-yl)}-{(4S,5S)-(5-methanesulfonyloxymethyl-2,2-dimethyl[1,3]dioxolan-4-yl)}-(S)methyl ester 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: 94.0%

: 3969-61-7
2,3,5,6-di-isopropyIidene-1,4-dihydroxy-D-mannitol

: 124-63-0
methanesulfonyl chloride

: 7115-24-4
(R)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]((4R,5R)-2,2-dimethyl-5-{[(methylsulfonyl)oxy]methyl}-1,3-dioxolan-4-yl)methyl methanesulfonate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1021/acs.jmedchem.7b00805

Reference yield:

: 7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4
2,3,5,6-di-O-isopropylidene-D-mannofuranose

: 124-63-0
methanesulfonyl chloride

: 7115-24-4
(R)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]((4R,5R)-2,2-dimethyl-5-{[(methylsulfonyl)oxy]methyl}-1,3-dioxolan-4-yl)methyl methanesulfonate

Guidance literature:: 2,3,5,6-di-O-isopropylidene-D-mannofuranose; With sodium tetrahydroborate; ethanol; at 20 ℃; for 4h;

methanesulfonyl chloride; With pyridine; dmap; at 0 ℃; for 3h; Inert atmosphere;

Reference yield:

: 7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4
2,3,5,6-di-O-isopropylidene-D-mannofuranose

: 7115-24-4
(R)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]((4R,5R)-2,2-dimethyl-5-{[(methylsulfonyl)oxy]methyl}-1,3-dioxolan-4-yl)methyl methanesulfonate

Guidance literature:: Multi-step reaction with 2 steps

1: sodium borohydride / methanol

2: 25 g / pyridine / CH₂Cl₂ / 6.5 h / 0 - 20 °C

With pyridine; sodium tetrahydroborate; In methanol; dichloromethane;
DOI:10.1139/V06-027