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Cas Database

627076-70-4

627076-70-4

Identification

  • Product Name:(R)-2-hydroxy-2-phenylpropyl 4-methylbenzenesulfonate

  • CAS Number: 627076-70-4

  • EINECS:

  • Molecular Weight:306.383

  • Molecular Formula: C16H18O4S

  • HS Code:

  • Mol File:627076-70-4.mol

Synonyms:(R)-2-hydroxy-2-phenylpropyl 4-methylbenzenesulfonate

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Relevant articles and documentsAll total 4 Articles be found

Absolute Configuration of α-Methylstyrene Oxide: The Correct Absolute Configuration/Optical Rotation Corelation

Archelas,Furstoss

, p. 6112 - 6114 (1999)

-

Absolute stereochemical determination of 1,2-diols via complexation with dinaphthyl borinic acid

Torabi Kohlbouni, Saeedeh,Sarkar, Aritra,Zhang, Jun,Li, Xiaoyong,Borhan, Babak

supporting information, p. 817 - 823 (2020/03/26)

Rapid derivatization of chiral 1,2-diols with dinaphthyl borinic acid (DBA) leads to a cyclic boronate, enabling the absolute stereochemical prediction via exciton-coupled circular dichroic (ECCD) of the naphthyl groups. Aryl- and alkyl-substituted 1,2-diols derivatized with DBA yield a predictable ECCD, which is also in agreement with theoretical predictions derived from computationally minimized structures.

Highly homogeneous stereocontrolled construction of quaternary hydroxyesters by addition of dimethylzinc to α-ketoesters promoted by chiral perhydrobenzoxazines and B(OEt)3

Infante, Rebeca,Nieto, Javier,Andres, Celia

, p. 4375 - 4379 (2012/05/20)

A highly efficient enantioselective addition of Me2Zn to α-ketoesters, assisted by a chiral perhydro-1,3-benzoxazine ligand, is described. This novel catalytic system offers homogeneous elevated enantioselectivities in the preparation of α-hydroxyesters that bear a quaternary stereocenter, with a minor dependence on electronic and steric effects when aromatic, heteroaromatic, or aliphatic α-ketoesters are employed. The catalyst can be recovered and reused without loss of activity.

A concise synthesis of (S)-(+)-1-(4-{2-[bis-(4-fluorophenyl)methoxy]-ethyl} piperazin-1-yl)-2-phenylpropan-2-ol dimaleate

Prisinzano, Thomas,Hsin, Ling-Wei,Folk, John E.,Flippen-Anderson, Judith L.,George, Clifford,Jacobson, Arthur E.,Rice, Kenner C.

, p. 3285 - 3289 (2007/10/03)

(S)-(+)-1-(4-{2-[Bis-(4-fluorophenyl)methoxy]-ethyl}piperazin-1-yl) -2-phenylpropan-2-ol dimaleate was prepared in several steps from (S)-(+)-atrolactic acid by a process permitting synthesis of multigram quantities. With the information provided by asymmetric synthesis, the X-ray crystal structure was solved.

Process route upstream and downstream products

Process route

(R)-1-phenyl-1,2-ethanediol
2406-22-6,4217-66-7,87760-50-7,35638-92-7

(R)-1-phenyl-1,2-ethanediol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

(R)-2-hydroxy-2-phenylpropyl 4-methylbenzenesulfonate
627076-70-4

(R)-2-hydroxy-2-phenylpropyl 4-methylbenzenesulfonate

Conditions
Conditions Yield
With dmap; triethylamine; In dichloromethane; at 0 ℃; for 16h; Inert atmosphere;
90%
With pyridine; at 0 ℃; for 6h;
87%
With pyridine; at 0 - 20 ℃;
phenylglyoxylic acid ethyl ester
1603-79-8

phenylglyoxylic acid ethyl ester

(R)-2-hydroxy-2-phenylpropyl 4-methylbenzenesulfonate
627076-70-4

(R)-2-hydroxy-2-phenylpropyl 4-methylbenzenesulfonate

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: triethyl borate; (1R,2R,4aS,7R,8aR,9aS)-2-isopropenyl-1-isopropyl-4,4,7-trimethyldecahydro-9-oxa-3a-azacyclopenta[b]naphthalen-1-ol / toluene / 20 h / -10 °C / Inert atmosphere
2: lithium aluminium tetrahydride / diethyl ether / 0.5 h / 0 °C / Inert atmosphere
3: dmap; triethylamine / dichloromethane / 16 h / 0 °C / Inert atmosphere
With dmap; lithium aluminium tetrahydride; triethyl borate; triethylamine; (1R,2R,4aS,7R,8aR,9aS)-2-isopropenyl-1-isopropyl-4,4,7-trimethyldecahydro-9-oxa-3a-azacyclopenta[b]naphthalen-1-ol; In diethyl ether; dichloromethane; toluene;
Multi-step reaction with 3 steps
1: triethyl borate; (1R,2R,4aS,7R,8aR,9aS)-2-isopropenyl-1-isopropyl-4,4,7-trimethyldecahydro-9-oxa-3a-azacyclopenta[b]naphthalen-1-ol / toluene / 20.5 h / -35 °C / Inert atmosphere
2: lithium aluminium tetrahydride / diethyl ether / 0.5 h / 0 °C / Inert atmosphere
3: dmap; triethylamine / dichloromethane / 16 h / 0 °C / Inert atmosphere
With dmap; lithium aluminium tetrahydride; triethyl borate; triethylamine; (1R,2R,4aS,7R,8aR,9aS)-2-isopropenyl-1-isopropyl-4,4,7-trimethyldecahydro-9-oxa-3a-azacyclopenta[b]naphthalen-1-ol; In diethyl ether; dichloromethane; toluene;
(R)-2-hydroxy-2-phenylpropyl 4-methylbenzenesulfonate
627076-70-4

(R)-2-hydroxy-2-phenylpropyl 4-methylbenzenesulfonate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: LiAlH4 / tetrahydrofuran / 2 h / 20 °C
2: pyridine / 0 - 20 °C
With pyridine; lithium aluminium tetrahydride; In tetrahydrofuran;
(R)-ethyl 2-hydroxy-2-phenylpropanoate
2406-23-7,32122-08-0,76496-51-0,29916-14-1

(R)-ethyl 2-hydroxy-2-phenylpropanoate

(R)-2-hydroxy-2-phenylpropyl 4-methylbenzenesulfonate
627076-70-4

(R)-2-hydroxy-2-phenylpropyl 4-methylbenzenesulfonate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / diethyl ether / 0.5 h / 0 °C / Inert atmosphere
2: dmap; triethylamine / dichloromethane / 16 h / 0 °C / Inert atmosphere
With dmap; lithium aluminium tetrahydride; triethylamine; In diethyl ether; dichloromethane;
methyl 2-oxo-2-phenylacetate
15206-55-0

methyl 2-oxo-2-phenylacetate

(R)-2-hydroxy-2-phenylpropyl 4-methylbenzenesulfonate
627076-70-4

(R)-2-hydroxy-2-phenylpropyl 4-methylbenzenesulfonate

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: (1R,2R,4aS,7R,8aR,9aS)-2-isopropenyl-1-isopropyl-4,4,7-trimethyldecahydro-9-oxa-3a-azacyclopenta[b]naphthalen-1-ol / toluene / 18.5 h / -35 °C / Inert atmosphere
2: lithium aluminium tetrahydride / diethyl ether / 0.5 h / 0 °C / Inert atmosphere
3: dmap; triethylamine / dichloromethane / 16 h / 0 °C / Inert atmosphere
With dmap; lithium aluminium tetrahydride; triethylamine; (1R,2R,4aS,7R,8aR,9aS)-2-isopropenyl-1-isopropyl-4,4,7-trimethyldecahydro-9-oxa-3a-azacyclopenta[b]naphthalen-1-ol; In diethyl ether; dichloromethane; toluene;
(R)-1-phenyl-1,2-ethanediol
2406-22-6,4217-66-7,87760-50-7,35638-92-7

(R)-1-phenyl-1,2-ethanediol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

(R)-2-hydroxy-2-phenylpropyl 4-methylbenzenesulfonate
627076-70-4

(R)-2-hydroxy-2-phenylpropyl 4-methylbenzenesulfonate

Conditions
Conditions Yield
With dmap; triethylamine; In dichloromethane; at 0 ℃; for 16h; Inert atmosphere;
90%
With pyridine; at 0 ℃; for 6h;
87%
With pyridine; at 0 - 20 ℃;
phenylglyoxylic acid ethyl ester
1603-79-8

phenylglyoxylic acid ethyl ester

(R)-2-hydroxy-2-phenylpropyl 4-methylbenzenesulfonate
627076-70-4

(R)-2-hydroxy-2-phenylpropyl 4-methylbenzenesulfonate

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: triethyl borate; (1R,2R,4aS,7R,8aR,9aS)-2-isopropenyl-1-isopropyl-4,4,7-trimethyldecahydro-9-oxa-3a-azacyclopenta[b]naphthalen-1-ol / toluene / 20 h / -10 °C / Inert atmosphere
2: lithium aluminium tetrahydride / diethyl ether / 0.5 h / 0 °C / Inert atmosphere
3: dmap; triethylamine / dichloromethane / 16 h / 0 °C / Inert atmosphere
With dmap; lithium aluminium tetrahydride; triethyl borate; triethylamine; (1R,2R,4aS,7R,8aR,9aS)-2-isopropenyl-1-isopropyl-4,4,7-trimethyldecahydro-9-oxa-3a-azacyclopenta[b]naphthalen-1-ol; In diethyl ether; dichloromethane; toluene;
Multi-step reaction with 3 steps
1: triethyl borate; (1R,2R,4aS,7R,8aR,9aS)-2-isopropenyl-1-isopropyl-4,4,7-trimethyldecahydro-9-oxa-3a-azacyclopenta[b]naphthalen-1-ol / toluene / 20.5 h / -35 °C / Inert atmosphere
2: lithium aluminium tetrahydride / diethyl ether / 0.5 h / 0 °C / Inert atmosphere
3: dmap; triethylamine / dichloromethane / 16 h / 0 °C / Inert atmosphere
With dmap; lithium aluminium tetrahydride; triethyl borate; triethylamine; (1R,2R,4aS,7R,8aR,9aS)-2-isopropenyl-1-isopropyl-4,4,7-trimethyldecahydro-9-oxa-3a-azacyclopenta[b]naphthalen-1-ol; In diethyl ether; dichloromethane; toluene;
(R)-2-hydroxy-2-phenylpropyl 4-methylbenzenesulfonate
627076-70-4

(R)-2-hydroxy-2-phenylpropyl 4-methylbenzenesulfonate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: LiAlH4 / tetrahydrofuran / 2 h / 20 °C
2: pyridine / 0 - 20 °C
With pyridine; lithium aluminium tetrahydride; In tetrahydrofuran;
(R)-ethyl 2-hydroxy-2-phenylpropanoate
2406-23-7,32122-08-0,76496-51-0,29916-14-1

(R)-ethyl 2-hydroxy-2-phenylpropanoate

(R)-2-hydroxy-2-phenylpropyl 4-methylbenzenesulfonate
627076-70-4

(R)-2-hydroxy-2-phenylpropyl 4-methylbenzenesulfonate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / diethyl ether / 0.5 h / 0 °C / Inert atmosphere
2: dmap; triethylamine / dichloromethane / 16 h / 0 °C / Inert atmosphere
With dmap; lithium aluminium tetrahydride; triethylamine; In diethyl ether; dichloromethane;
methyl 2-oxo-2-phenylacetate
15206-55-0

methyl 2-oxo-2-phenylacetate

(R)-2-hydroxy-2-phenylpropyl 4-methylbenzenesulfonate
627076-70-4

(R)-2-hydroxy-2-phenylpropyl 4-methylbenzenesulfonate

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: (1R,2R,4aS,7R,8aR,9aS)-2-isopropenyl-1-isopropyl-4,4,7-trimethyldecahydro-9-oxa-3a-azacyclopenta[b]naphthalen-1-ol / toluene / 18.5 h / -35 °C / Inert atmosphere
2: lithium aluminium tetrahydride / diethyl ether / 0.5 h / 0 °C / Inert atmosphere
3: dmap; triethylamine / dichloromethane / 16 h / 0 °C / Inert atmosphere
With dmap; lithium aluminium tetrahydride; triethylamine; (1R,2R,4aS,7R,8aR,9aS)-2-isopropenyl-1-isopropyl-4,4,7-trimethyldecahydro-9-oxa-3a-azacyclopenta[b]naphthalen-1-ol; In diethyl ether; dichloromethane; toluene;

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