57495-46-2

Basic information

• Product Name: (-)-1 4-DI-O-TOSYL-L-THREITOL
• Synonyms: L-THREITOL 1,4-DI-P-TOSYLATE;(-)-1 4-DI-O-TOSYL-L-THREITOL;[2,3-dihydroxy-4-(4-methylphenyl)sulfonyloxy-butyl] 4-methylbenzenesulfonate;[2,3-dihydroxy-4-(4-methylphenyl)sulfonyloxybutyl] 4-methylbenzenesulfonate;4-methylbenzenesulfonic acid [2,3-dihydroxy-4-(4-methylphenyl)sulfonyloxy-butyl] ester;L-Threitol-1,4-ditosylate
• CAS NO: 57495-46-2
• Molecular Formula: C₁₈H₂₂O₈S₂
• Molecular Weight: 430.49
• Mol File: 57495-46-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 657.6°Cat760mmHg
• Flash Point: 351.5°C
• Appearance: /
• Density: 1.397g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.586
• Solubility: DCM, Ethyl Acetate
• CAS DataBase Reference: (-)-1 4-DI-O-TOSYL-L-THREITOL(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-1 4-DI-O-TOSYL-L-THREITOL(57495-46-2)
• EPA Substance Registry System: (-)-1 4-DI-O-TOSYL-L-THREITOL(57495-46-2)

Safety Data

• Hazardous Substances Data: 57495-46-2(Hazardous Substances Data)

Usage

Uses

L-Threitol-1,4-ditosylate is a tosyl protected L-Threitol (T400000), an intermediate used to synthesize novel aza-sugar-based metalloproteinase MMP/ADAM inhibitors.

InChI:InChI=1/C18H22O8S2/c1-13-3-7-15(8-4-13)27(21,22)25-11-17(19)18(20)12-26-28(23,24)16-9-5-14(2)6-10-16/h3-10,17-20H,11-12H2,1-2H3/t17-,18-/m1/s1

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 37002-45-2 (4S,5S)-2,2-dimethyl-4,5-bis(p-toluenesulfonyloxymethyl)-1,3-dioxolan 

Downstream Products

• 158835-58-6 (S,S)-2,3-bis(O-trimethylsilyl)-1,4-bisbutane-1,2,3,4-tetrol 
• 158835-60-0 (S,S)-2-methyl-2-phenyl-4,5-bis(p-toluenesulfonyloxymethyl)-1,3-dioxolane 
• 158835-61-1 (S,S)-2-(hydroxymethyl)-2-phenyl-4,5-bis(p-toluenesulfonyloxymethyl)-1,3-dioxolane 
• 158835-59-7 (S,S)-2-(acetoxymethyl)-2-phenyl-4,5-bis(p-toluenesulfonyloxymethyl)-1,3-dioxolane 
• 158835-62-2 (4S,5S,2'rac)-2-phenyl-2-<(tetrahydropyran-2'-yl)oxymethyl>-4,5-bis(p-toluenesulfonyloxymethyl)-1,3-dioxolane 
• 171561-22-1 (S,S)-2-(acetoxymethyl)-2-methyl-4,5-bis(p-toluenesulfonyloxymethyl)-1,3-dioxolane 
• 171561-23-2 (S,S)-2-(2'-acetoxyphenyl)-4,5-bis(p-toluenesulfonyloxymethyl)-1,3-dioxolane 
• 220358-43-0 (3S,4S)-N-(o-iodobenzyl)pyrrolidine-3,4-diol 
• 90365-74-5 (3S,4S)-(+)-1-benzyl-3,4-pyrrolidinediol 
• 298-18-0 (S,S)-diepoxybutane 
• 19132-06-0 (2S,3S)-butane-2,3-diol 
• 126299-18-1 C₂₇H₃₈O₁₂S₂ 
• 126299-10-3 C₂₅H₃₄O₁₁S₂ 

Relevant articles and documents

Synthesis of chiral hydroxythiolanes as potential catalysts for asymmetric organozinc additions to carbonyl compounds

Optically active 3-hydroxythiolane was stereospecifically synthesized from L-aspartic acid and oxidized to give both diastereomeric S-oxides, which were chromatographicatly separated and their configuration was determined. Starting from natural (+)-(R,R)-tartaric acid, C2-symmetric trans-(R,R)-3,4-dihydroxythiolane was stereospecifically synthesized for the first time. Some of its monofunctionalized derivatives as well as its S-oxide were also obtained and characterized. meso-cis-3,4-Dihydroxythiolane was obtained in a similar way from meso-tartaric acid and subjected to desymmetrization either by a lipase-promoted acetylation or hydrolysis of the corresponding O, O'-diacetyl derivative, to give a chiral monoacetate with ee up to 36%. After its oxidation two diastereomeric sulfoxides were obtained which were separated by chromatography. The crystalline one was subjected to X-ray analysis and its absolute configuration was determined as 1S, 3S, 4R. All the optically active products were checked as potential catalysts for asymmetric addition of diethylzinc to benzaldehyde. However, they proved to have a very low catalytic activity: yields of the products were in the range 10-90% but ee only up to 10%. A conclusion was drawn that in this type of reaction neither is the hydroxy sulfide (sulfoxide) moiety capable of properly binding diethylzinc, nor does the sulfinyl group exert its normal stereoinduction.

A NEW APPROACH TO THE SYNTHESIS OF (-)-2,3-O-ISOPROPYLIDENE-2,3-DIHYDROXY-1,4-BIS(DIPHENYLPHOSPHINO)BUTANE(DIOP)

(-)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane (DIOP) has been prepared by reaction of (-)-1,2:3,4-diepoxybutane with lithium diphenylphosphide followed by ketalisation with 2,2-dimethoxypropane.