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(+)-1,4-Di-o-tosyl-2,3-o-isopropylidene-d-threitol

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Name

(+)-1,4-Di-o-tosyl-2,3-o-isopropylidene-d-threitol

EINECS 256-943-5
CAS No. 51064-65-4 Density 1.275 g/cm3
PSA 121.96000 LogP 5.09590
Solubility N/A Melting Point 90-92 °C
Formula C21H26O8S2 Boiling Point 608.3 °C at 760 mmHg
Molecular Weight 470.565 Flash Point 321.7 °C
Transport Information N/A Appearance beige
Safety 22-24/25 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 51064-65-4 ((+)-1,4-Di-o-tosyl-2,3-o-isopropylidene-d-threitol) Hazard Symbols IrritantXi
Synonyms

(4R,5R)-4,5-Bis[[[(4-methylphenyl)sulfonyl]oxy]methyl]-2,2-dimethyl-[1,3]dioxolane;1,4-Ditosyl-2,3-O-isopropylidene-D-threitol;2,3-Isopropylidene-D-threitol-1,4-ditosylate;

Article Data 13

(+)-1,4-Di-o-tosyl-2,3-o-isopropylidene-d-threitol Specification

The CAS registry number of 1,3-Dioxolane-4,5-dimethanol,2,2-dimethyl-,4,5-bis(4-methylbenzenesulfonate),(4R,5R)- is 51064-65-4. The IUPAC name is [(4R,5R)-2,2-dimethyl-5-[(4-methylphenyl)sulfonyloxymethyl]-1,3-dioxolan-4-yl]methyl 4-methylbenzenesulfonate. Its EINECS registry number is 256-943-5. In addition, the molecular formula is C21H26O8S2 and the molecular weight is 470.56. It is a kind of white to light yellow crystal powder and belongs to the classes of Chiral; Biochemistry; Dioxanes & Dioxolanes; Dioxolanes; O-Substituted Sugars; Sugar Alcohols; Sugars.

Physical properties about this chemical are: (1)ACD/LogP: 3.03; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.03; (4)ACD/LogD (pH 7.4): 3.03; (5)ACD/BCF (pH 5.5): 118.17; (6)ACD/BCF (pH 7.4): 118.17; (7)ACD/KOC (pH 5.5): 1059.5; (8)ACD/KOC (pH 7.4): 1059.5; (9)#H bond acceptors: 8; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 121.96 Å2; (13)Index of Refraction: 1.539; (14)Molar Refractivity: 115.65 cm3; (15)Molar Volume: 368.9 cm3; (16)Polarizability: 45.84×10-24cm3; (17)Surface Tension: 41.7 dyne/cm; (18)Density: 1.275 g/cm3; (19)Flash Point: 321.7 °C; (20)Enthalpy of Vaporization: 87.06 kJ/mol; (21)Boiling Point: 608.3 °C at 760 mmHg; (22)Vapour Pressure: 4.31E-14 mmHg at 25°C.

Preparation of 1,3-Dioxolane-4,5-dimethanol,2,2-dimethyl-,4,5-bis(4-methylbenzenesulfonate),(4R,5R)-: it can be prepared by O2,O3-isopropylidene-D-threitol and toluene-4-sulfonyl chloride. This reaction will need reagent NEt3 and solvent diethyl ether. The reaction time is 17 hours at reaction temperature of 30 °C. The yield is about 85%.

1,3-Dioxolane-4,5-dimethanol,2,2-dimethyl-,4,5-bis(4-methylbenzenesulfonate),(4R,5R)- can be prepared by O2,O3-isopropylidene-D-threitol and toluene-4-sulfonyl chloride

Uses of 1,3-Dioxolane-4,5-dimethanol,2,2-dimethyl-,4,5-bis(4-methylbenzenesulfonate),(4R,5R)-: it can react with bis(4-methoxy-3,5-dimethylphenyl)phosphine to get (4S,5S)-(-)-4,5-bis[bis(4'-methoxy-3',5'-dimethyl-phenyl)phosphinomethyl]-2,2-dimethyl-1,3-dioxolane. This reaction will need reagent n-BuLi and solvent tetrahydrofuran. The yield is about 65%.

1,3-Dioxolane-4,5-dimethanol,2,2-dimethyl-,4,5-bis(4-methylbenzenesulfonate),(4R,5R)- can react with bis(4-methoxy-3,5-dimethylphenyl)phosphine to get (4S,5S)-(-)-4,5-bis[bis(4'-methoxy-3',5'-dimethyl-phenyl)phosphinomethyl]-2,2-dimethyl-1,3-dioxolan
1,3-Dioxolane-4,5-dimethanol,2,2-dimethyl-,4,5-bis(4-methylbenzenesulfonate),(4R,5R)- can react with bis(4-methoxy-3,5-dimethylphenyl)phosphine to get (4S,5S)-(-)-4,5-bis[bis(4'-methoxy-3',5'-dimethyl-phenyl)phosphinomethyl]-2,2-dimethyl-1,3-dioxolan

When you are using this chemical, please be cautious about it as the following:
It irritates to eyes, respiratory system and skin. Therefore, you should not breathe dust. And you should avoid contact with skin and eyes.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: O=S(=O)(OC[C@H]2OC(O[C@@H]2COS(=O)(=O)c1ccc(cc1)C)(C)C)c3ccc(cc3)C
(2)InChI: InChI=1/C21H26O8S2/c1-15-5-9-17(10-6-15)30(22,23)26-13-19-20(29-21(3,4)28-19)14-27-31(24,25)18-11-7-16(2)8-12-18/h5-12,19-20H,13-14H2,1-4H3/t19-,20-/m1/s1
(3)InChIKey: KPFDKWNWYAXRNJ-WOJBJXKFBV

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