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16355-00-3

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16355-00-3 Usage

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 16355-00-3 differently. You can refer to the following data:
1. (R)-(-)-1-Phenyl-1,2-ethanediol is an intermediate for the synthesis of enantiopure substituted 1,4-Dioxanes. Extremely valuable and versatile alcohol used as a chiral building block in organic synthesis.
2. Intermediate for the synthesis of chiral phosphine catalysts for asymmetric hydrogenations.

Purification Methods

Purify the diol by recrystallisation from *C6H6/ligroin and sublime it at 1-2mm. [Arpesella et al. Gazetta 85 1354 1955, Prelog et al. Helv Chim Acta 37 221 1954, Beilstein 6 IV 5939.]

Check Digit Verification of cas no

The CAS Registry Mumber 16355-00-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,6,3,5 and 5 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 16355-00:
(7*1)+(6*6)+(5*3)+(4*5)+(3*5)+(2*0)+(1*0)=93
93 % 10 = 3
So 16355-00-3 is a valid CAS Registry Number.
InChI:InChI=1/C8H10O2/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8-10H,6H2/t8-/m0/s1

16355-00-3 Well-known Company Product Price

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  • TCI America

  • (P1150)  (R)-(-)-1-Phenylethane-1,2-diol  >98.0%(GC)

  • 16355-00-3

  • 1g

  • 350.00CNY

  • Detail
  • TCI America

  • (P1150)  (R)-(-)-1-Phenylethane-1,2-diol  >98.0%(GC)

  • 16355-00-3

  • 5g

  • 990.00CNY

  • Detail
  • TCI America

  • (P1150)  (R)-(-)-1-Phenylethane-1,2-diol  >98.0%(GC)

  • 16355-00-3

  • 25g

  • 3,250.00CNY

  • Detail
  • Alfa Aesar

  • (L10494)  (R)-(-)-Phenyl-1,2-ethanediol, 99%   

  • 16355-00-3

  • 250mg

  • 209.0CNY

  • Detail
  • Alfa Aesar

  • (L10494)  (R)-(-)-Phenyl-1,2-ethanediol, 99%   

  • 16355-00-3

  • 1g

  • 361.0CNY

  • Detail
  • Aldrich

  • (302163)  (R)-(−)-1-Phenyl-1,2-ethanediol  99%

  • 16355-00-3

  • 302163-1G

  • 875.16CNY

  • Detail

16355-00-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name (R)-(?)-1-Phenyl-1,2-ethanediol

1.2 Other means of identification

Product number -
Other names (R)-(-)-1-Phenylethane-1,2-diol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:16355-00-3 SDS

16355-00-3Synthetic route

1-phenyl-2-hydroxyethanone
582-24-1

1-phenyl-2-hydroxyethanone

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

Conditions
ConditionsYield
With β-D-glucose In aq. phosphate buffer at 35℃; for 24h; pH=7.5; Kinetics; Temperature; pH-value; Solvent; Reagent/catalyst; Enzymatic reaction;99.9%
With cobalt(II) acetate; C31H31N2OP In tetrahydrofuran at 25℃; for 1h; Reagent/catalyst; Inert atmosphere;97%
With hydrogen; chiral iridium(III) complex In methanol at 60℃; under 7600.51 Torr; for 15h;94%
phenylglyoxal hydrate
1074-12-0

phenylglyoxal hydrate

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

Conditions
ConditionsYield
With D-glucose; D-glucose dehydrogenase; β-nicotinamide adenine dinucleotide 2'-phosphate reduced tetra(cyclohexylammonium) salt; carbonyl reductase from Pichia pastoris GS115; sodium hydroxide In aq. phosphate buffer; dimethyl sulfoxide at 20℃; for 12h; pH=6.5; Enzymatic reaction;99%
styrene
292638-84-7

styrene

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

Conditions
ConditionsYield
With 1,4-bis(9-O-dihydroquinidine)phthalazine In water; tert-butyl alcohol at 20℃; for 2h; Sharpless asymmetric dihydroxylation;98%
With potassium osmate(VI) dihydrate; cetyltrimethylammonim bromide; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III) In water at 20℃; for 48h; Sharpless dihydroxylation; optical yield given as %ee;98%
With water; potassium carbonate; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane]; potassium hexacyanoferrate(III) In tert-butyl alcohol for 6h; Reagent/catalyst; enantioselective reaction;98%
(1R)-2-({[(1S)-2,2-dimethyl-1-phenylpropyl]amino}oxy)ethanol
757195-36-1

(1R)-2-({[(1S)-2,2-dimethyl-1-phenylpropyl]amino}oxy)ethanol

A

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

B

(1S)-α-(1,1-dimethylethyl)benzenemethanamine
82729-98-4

(1S)-α-(1,1-dimethylethyl)benzenemethanamine

Conditions
ConditionsYield
With hexacarbonyl molybdenum In water; acetonitrile at 85℃; for 1h;A n/a
B 98%
(R)-methyl mandelate
20698-91-3

(R)-methyl mandelate

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 20℃; for 0.5h;97%
With lithium aluminium tetrahydride74%
Stage #1: (R)-methyl mandelate With lithium aluminium tetrahydride In 1,2-dimethoxyethane at 20℃; for 12h; Elimination;
Stage #2: With hydrogenchloride; ammonium chloride Hydrolysis; Further stages.;
70%
styrene oxide
96-09-3

styrene oxide

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

Conditions
ConditionsYield
With E. coli/(recombinant Vigna radiata epoxide hydrolase VrEH3) whole cells In methanol; aq. phosphate buffer at 25℃; for 7h; pH=7.0; pH-value; Temperature; Microbiological reaction; enantioselective reaction;97%
With tris paraperiodate; water In acetonitrile for 0.0833333h; Ambient temperature;90%
With epoxide hydrolase from Vigna radiata; variant VrEH2M263V In aq. phosphate buffer; dimethyl sulfoxide at 30℃; for 1.5h; pH=7; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;90%
styrene
292638-84-7

styrene

A

styrene oxide
96-09-3

styrene oxide

B

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

C

(S)-1-phenyl-1,2-ethanediol
25779-13-9

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

Conditions
ConditionsYield
With styrene monooxygenase In Hexadecane for 24h; aq. buffer; optical yield given as %ee;A 97%
B n/a
C n/a
styrene oxide
96-09-3

styrene oxide

A

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

B

(S)-styrene oxide
20780-54-5

(S)-styrene oxide

Conditions
ConditionsYield
Stage #1: styrene oxide With water; 4-nitro-benzoic acid; [(S,S)-N,N’-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(II) at 20℃; Acidic aqueous solution;
Stage #2: With ammonia at 20℃; for 1h;
A 95.3%
B 67.9%
With Aspergillus niger epoxide hydrolases immobilized onto modified Eupergit C In aq. phosphate buffer; dimethyl sulfoxide at 25℃; for 4h; pH=6.5; Kinetics; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;A n/a
B 48%
With [(S,S)-N,N’-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(II); water In dichloromethane; acetonitrile at 20℃; for 144h; Resolution of racemate;A n/a
B 47%
1-phenyl-2-hydroxyethanone
582-24-1

1-phenyl-2-hydroxyethanone

A

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

B

(S)-1-phenyl-1,2-ethanediol
25779-13-9

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

Conditions
ConditionsYield
With cobalt(II) acetate; C31H31N2OP In tetrahydrofuran at 25℃; for 1h; Reagent/catalyst; Inert atmosphere;A 95%
B n/a
With diisobutylaluminium hydride; (S)-1-methyl-2-<(piperidin-1-yl)-methyl>pyrrolidine; tin(ll) chloride In dichloromethane at -100℃; for 0.333333h; Product distribution; asymmetric reduction of prochiral hydroxy ketones;
With baker yeast Product distribution; Thermodynamic data; ee = 99.19percent, ΔΔG(excit.)298 = 3.26+/-0.06 kcal/mol;
(R)-2-hydroxy-2-phenylethyl acetate
147256-18-6

(R)-2-hydroxy-2-phenylethyl acetate

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

Conditions
ConditionsYield
With potassium carbonate In methanol for 4h;95%
With potassium carbonate In methanol for 4h;94%
(1R)-2-{[(S)-[(2-(methoxymethoxy)phenyl)(phenyl)methyl]amino]oxy}-1-phenylethanol
757195-42-9

(1R)-2-{[(S)-[(2-(methoxymethoxy)phenyl)(phenyl)methyl]amino]oxy}-1-phenylethanol

A

(1S)-1-[2-(methoxymethoxy)phenyl](phenyl)methanamine

(1S)-1-[2-(methoxymethoxy)phenyl](phenyl)methanamine

B

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

Conditions
ConditionsYield
With hexacarbonyl molybdenum In water; acetonitrile at 85℃; for 1h;A 95%
B n/a
styrene
292638-84-7

styrene

Resin-OsO4

Resin-OsO4

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

Conditions
ConditionsYield
94%
94%
94%
styrene oxide
96-09-3

styrene oxide

A

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

B

(S)-1-phenyl-1,2-ethanediol
25779-13-9

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

Conditions
ConditionsYield
With Escherichia coli Rosetta(DE3)/epoxide hydrolase from Glycine max wet cells In aq. phosphate buffer at 25℃; pH=7; Catalytic behavior; Microbiological reaction; Resolution of racemate; Enzymatic reaction; enantioselective reaction;A 93.8%
B n/a
With water at 37℃; rabbit liver microsomal epoxide hydrolase; Yields of byproduct given. Title compound not separated from byproducts;
With water In ethanol Beauveria sulfurescens; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
(R)-2,2-dimethyl-4-phenyl-1,3-dioxolane
147441-61-0

(R)-2,2-dimethyl-4-phenyl-1,3-dioxolane

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

Conditions
ConditionsYield
zirconium(IV) chloride In methanol at 35℃; for 3h;93%
(R)-(-)-2-tert-butoxy-2-oxo-1-phenylethyl pyrrolidine-1-carboxylate
1041400-13-8

(R)-(-)-2-tert-butoxy-2-oxo-1-phenylethyl pyrrolidine-1-carboxylate

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at -78 - 20℃; Inert atmosphere;92%
(2S,5R)-2-(2-chlorophenyl)-5-phenyl-3-tosyloxazolidin-4-one
1258406-85-7

(2S,5R)-2-(2-chlorophenyl)-5-phenyl-3-tosyloxazolidin-4-one

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Inert atmosphere;92%
(1R)-2-[({(1S)-1-[2-(methoxymethoxy)phenyl]ethyl}amino)oxy]-1-phenylethanol
757195-48-5

(1R)-2-[({(1S)-1-[2-(methoxymethoxy)phenyl]ethyl}amino)oxy]-1-phenylethanol

A

(1S)-1-[2-(methoxymethoxy)phenyl]ethanamine
757195-50-9

(1S)-1-[2-(methoxymethoxy)phenyl]ethanamine

B

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

Conditions
ConditionsYield
With hexacarbonyl molybdenum In water; acetonitrile at 85℃; for 1h;A 91%
B n/a
(R)-(-)-1-phenylethane-1,2-diol dipropionate
144688-34-6

(R)-(-)-1-phenylethane-1,2-diol dipropionate

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

Conditions
ConditionsYield
With sodium hydroxide In methanol at 25℃; for 3h;90%
(R)-2-methylcarbonyloxy-1-phenylethyl acetate
78692-90-7

(R)-2-methylcarbonyloxy-1-phenylethyl acetate

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

Conditions
ConditionsYield
zirconium(IV) chloride In methanol at 35℃; for 4h;90%
With potassium carbonate In methanol at 20℃; for 4h;
(4S,1'R,2'R)-N-(3)-[1'-(m-chlorobenzoyl)-2-hydroxy-2'-phenylethan-1'yl]-4-phenyl-5,5-dimethyloxazolidin-2-one
1067232-57-8

(4S,1'R,2'R)-N-(3)-[1'-(m-chlorobenzoyl)-2-hydroxy-2'-phenylethan-1'yl]-4-phenyl-5,5-dimethyloxazolidin-2-one

A

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

B

(4S)-5,5-dimethyl-4-phenyl-1,3-oxazolidin-2-one
168297-84-5

(4S)-5,5-dimethyl-4-phenyl-1,3-oxazolidin-2-one

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol for 0.166667h;A 60%
B 90%
styrene
292638-84-7

styrene

A

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

B

(S)-1-phenyl-1,2-ethanediol
25779-13-9

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

Conditions
ConditionsYield
With potassium dioxotetrahydroxoosmate(VI); potassium carbonate; potassium hexacyanoferrate(III); methanesulfonamide; DHQD-PHAL-OPEG-OMe In water; tert-butyl alcohol at 0℃; for 24h; Title compound not separated from byproducts;A 87%
B n/a
With osmium(VIII) oxide; lithium aluminium tetrahydride; MEQ-DHQD Thermodynamic data; Kinetics; 1) toluene, 2) THF, 30 min, RT; influence of the reaction temperature on the enantioselectivity of the asymmetric dihydroxylation of different olefins with other reagents, investigations of the ee-values;
With potassium dioxotetrahydroxoosmate(VI); iodine; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine In water; tert-butyl alcohol at 0℃; for 27h; Product distribution; Mechanism; electrolysis; various co-oxidants; asymmetric dihydroxylation; further cond.: chemical method;
(R)-Styrene oxide
20780-53-4

(R)-Styrene oxide

A

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

B

(S)-1-phenyl-1,2-ethanediol
25779-13-9

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

Conditions
ConditionsYield
With Tris-HCl buffer; Sphingomonas sp. HXN-200 cell free extract In hexane at 25℃; for 4h; pH=7.5; Title compound not separated from byproducts;A 87%
B 13%
With water; potassium hydroxide at 30℃; for 288h; Product distribution; Mechanism; other pH;
With sodium phosphate buffer; enzymatic extract of S. racemosum In dimethyl sulfoxide at 27℃; Rate constant; Mechanism; Product distribution; regioselectivity of the biohydrolysis;
(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
173603-23-1

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

Conditions
ConditionsYield
Stage #1: (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) With hydrogen; di(norbornadiene)rhodium(I) tetrafluoroborate; (R)-1-[2-(2'-diphenylphosphinophenyl)-ferrocenyl]ethyldi[bis-(3,5-trifluoromethyl)phenyl]phosphine under 11400.8 Torr;
Stage #2: With dihydrogen peroxide Product distribution / selectivity;
86%
Stage #1: (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) With hydrogen; di(norbornadiene)rhodium(I) tetrafluoroborate; (R)-1-[2-(2'-diphenylphosphinophenyl)-ferrocenyl]ethyldi[bis-(3,5-trifluoromethyl)phenyl]phosphine under 11400.8 Torr;
Stage #2: With sodium hydroxide; dihydrogen peroxide Product distribution / selectivity;
86%
4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

A

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

B

(4S)-4-phenyl[1,3]dioxolan-2-one
4427-92-3, 90971-11-2, 129097-94-5, 90970-80-2

(4S)-4-phenyl[1,3]dioxolan-2-one

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; Kinetics; pig liver esterase, phosphate buffer pH 7.4;A 85%
B n/a
In dimethyl sulfoxide at 20℃; pig liver esterase, phosphate buffer pH 7.4; Yields of byproduct given;A 85%
B n/a
(R)-Mandelic Acid
611-71-2

(R)-Mandelic Acid

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether 1.) reflux, 5 h, 2.) RT, 12 h;85%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2.5h; Inert atmosphere;71%
With lithium aluminium tetrahydride In diethyl ether for 6h; Reduction; Heating;70%
(1R)-1-phenyl-2-({[(1S)-1-phenylpentyl]amino}oxy)ethanol
757195-34-9

(1R)-1-phenyl-2-({[(1S)-1-phenylpentyl]amino}oxy)ethanol

A

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

B

(1S)-1-amino-1-phenylpentane
105370-60-3

(1S)-1-amino-1-phenylpentane

Conditions
ConditionsYield
With hexacarbonyl molybdenum In water; acetonitrile at 85℃; for 1h;A n/a
B 85%
(1R)-1-phenyl-2-({[(1S)-1-phenyl-2-propenyl]amino}oxy)ethanol
757195-40-7

(1R)-1-phenyl-2-({[(1S)-1-phenyl-2-propenyl]amino}oxy)ethanol

A

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

B

(1S)-1-phenyl-2-propen-1-amine
244092-75-9

(1S)-1-phenyl-2-propen-1-amine

Conditions
ConditionsYield
With zinc In tetrahydrofuran; water; acetic acid at 60℃; for 4h;A n/a
B 83%
(1R)-1-phenyl-2-({[(1S)-1-phenylethyl]amino}oxy)ethanol
757195-26-9

(1R)-1-phenyl-2-({[(1S)-1-phenylethyl]amino}oxy)ethanol

A

(S)-1-phenyl-ethylamine
2627-86-3

(S)-1-phenyl-ethylamine

B

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

Conditions
ConditionsYield
With hexacarbonyl molybdenum In water; acetonitrile at 85℃; for 1h;A 80%
B n/a
(R)-1-phenyl-2-(α,α-diphenylbenzyloxy)ethyl-3,4-di-O-benzyl-2-deoxy-6-O-(α,α-diphenylbenzyl)-L-glucoside
179924-50-6

(R)-1-phenyl-2-(α,α-diphenylbenzyloxy)ethyl-3,4-di-O-benzyl-2-deoxy-6-O-(α,α-diphenylbenzyl)-L-glucoside

A

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

B

3,4-di-O-benzyl-2-deoxy-L-glucopyranose

3,4-di-O-benzyl-2-deoxy-L-glucopyranose

Conditions
ConditionsYield
In tetrahydrofuran; hydrogenchloride Hydrolysis;A 2.37 g
B 78%
phenylethane 1,2-diol
93-56-1

phenylethane 1,2-diol

A

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

B

(S)-1-phenyl-1,2-ethanediol
25779-13-9

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

Conditions
ConditionsYield
With cell free extract from Candida parapsilosis CICC 1627 In aq. phosphate buffer at 30℃; for 48h; pH=6.5; Reagent/catalyst; Microbiological reaction; enantioselective reaction;A n/a
B 78%
With MCCD-HPS packed column In hydrogenchloride; acetonitrile pH=8.6;
With halohydrin dehydro-dehalogenase from Alcaligenes sp. DS-S-7G; 2,6-Dichlorophenolindophenol; phenazine methosulfate Enzymatic reaction; Title compound not separated from byproducts.;
(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

(R)-4-Phenyl-[1,3,2]dioxathiolane 2-oxide
133522-24-4

(R)-4-Phenyl-[1,3,2]dioxathiolane 2-oxide

Conditions
ConditionsYield
With thionyl chloride In tetrachloromethane Heating;100%
With thionyl chloride Heating;79%
With thionyl chloride In dichloromethane Yield given;
(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(R)-2-(tert-butyldimethylsilyloxy)-1-phenylethan-1-ol
110743-96-9

(R)-2-(tert-butyldimethylsilyloxy)-1-phenylethan-1-ol

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 0 - 20℃; for 1.5h; Inert atmosphere;100%
With dmap; triethylamine In dichloromethane for 4h; Inert atmosphere;98%
With dmap; triethylamine In dichloromethane at 20℃; for 2h;91%
With dmap; triethylamine In dichloromethane at 20℃; for 2h;87%
(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

(R)-phenyl-1,2-bis(methanesulfonyloxy)ethane
278169-72-5

(R)-phenyl-1,2-bis(methanesulfonyloxy)ethane

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
With triethylamine In dichloromethane at 0 - 20℃;
With triethylamine In dichloromethane
Stage #1: (R)-1-phenyl-1,2-ethanediol With triethylamine In dichloromethane at 0℃; for 0.166667h;
Stage #2: methanesulfonyl chloride In dichloromethane at 20℃; for 5h;
(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride
39637-99-5, 20445-33-4

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride

(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (R)-1-phenyl-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-ethyl ester

(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (R)-1-phenyl-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-ethyl ester

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 18h;99%
With pyridine; 1-amino-3-(dimethylamino)propane In dichloromethane for 0.416667h;
(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

ortho-diphenylphosphinobenzoic acid
17261-28-8

ortho-diphenylphosphinobenzoic acid

(R)-2-hydroxy-2-phenylethyl 2-(diphenylphosphino)-benzoate
1220999-80-3

(R)-2-hydroxy-2-phenylethyl 2-(diphenylphosphino)-benzoate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 24h; Inert atmosphere;98%
(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

(R)-Mandelic Acid
611-71-2

(R)-Mandelic Acid

Conditions
ConditionsYield
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide In acetone at 0℃; pH=8.3; chemoselective reaction;96%
With recombinant alditol oxidase from Streptomyces coelicolor A3(2); catalase from bovine liver at 25℃; pH=7.5; Kinetics; Reagent/catalyst; Temperature; pH-value; aq. phosphate buffer; Enzymatic reaction; enantioselective reaction;
carbon dioxide
124-38-9

carbon dioxide

(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

(R)-1-phenyl-1,2-ethanediol carbonate
90971-11-2

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

Conditions
ConditionsYield
With 1-butyl-3-methylimidazolium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene at 70℃; under 7500.75 Torr; for 18h;96%
(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

(R)-2-hydroxy-2-phenylethyl 4-methylbenzenesulfonate
40434-87-5

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

Conditions
ConditionsYield
With di(n-butyl)tin oxide; triethylamine In dichloromethane at 0 - 20℃; for 3h;92.2%
With pyridine at 0 - 20℃; Inert atmosphere;78%
With pyridine at -10℃; for 4h;76%
(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

chloromethyldiphenylsilane
144-79-6

chloromethyldiphenylsilane

1,2-bis(diphenylmethylsilyloxy)-1-phenylethane

1,2-bis(diphenylmethylsilyloxy)-1-phenylethane

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 3h; Inert atmosphere;90%
(R)-1-phenyl-1,2-ethanediol
16355-00-3

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

4-biphenylboronic acid
5122-94-1

4-biphenylboronic acid

(R)-(-)-2-(4-biphenyl)-4-phenyl-1,3,2-dioxaborolane

(R)-(-)-2-(4-biphenyl)-4-phenyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
In chloroform at 20℃;89%
With 4 A molecular sieve In chloroform at 20℃;89%

16355-00-3Relevant articles and documents

One Pot Asymmetric Synthesis of (R)-Phenylglycinol from Racemic Styrene Oxide via Cascade Biocatalysis

Sun, Zai-Bao,Zhang, Zhi-Jun,Li, Fu-Long,Nie, Yao,Yu, Hui-Lei,Xu, Jian-He

, p. 3802 - 3807 (2019)

(R)-Phenylglycinol is an important chiral building block for pharmaceutical and fine chemical industry, and its efficient synthesis from cheap and commercially available starting materials is challenging and highly desirable. Herein, a new three-step one-pot cascade system employing epoxide hydrolase, glycerol dehydrogenase, and ω-transaminase was designed for the asymmetric synthesis of (R)-phenylglycinol from racemic styrene oxide. A cofactor self-sufficient system employing AlaDH/L?Ala was utilized for the regeneration of expensive cofactor NAD+ and removal of by-product pyruvate. Furthermore, in situ product removal by cation resin adsorption was used to drive the thermodynamic equilibrium of the cascade reaction to the direction of product generation. Finally, optically pure (R)-phenylglycinol was successfully produced from racemic styrene oxide with high yield (81.9 %) and excellent enantioselectivity (99 % ee).

A Comparison of Ligands Proposed for the Asymmetric Dihydroxylation

Crispino, Gerard A.,Makita, Atsushi,Wang, Zhi-Min,Sharpless, K. Barry

, p. 543 - 546 (1994)

Comparative data for several ligands proposed recently for use in the osmium-catalyzed asymmetric dihydroxylation (AD) are presented.

Stereochemistry of the Spontaneous, Acid-Catalyzed and Base Catalyzed Hydrolyses of Styrene Oxide

Lin, Bin,Whalen, Dale L.

, p. 1638 - 1641 (1994)

The stereochemical courses of the spontaneous, hydronium ion-catalyzed and hydroxide ion-catalyzed hydrolyses of (R)-styrene oxide have been determined by 1H NMR analysis of the bis-(+)-α-(methoxy-α-trifluoromethyl)phenylacetate diesters of the styrene glycol products from each reaction.The glycol product from the spontaneous reaction of chiral styrene oxide is the result of 93percent inversion and 7percent retention.This result, coupled with published results of 18O-labeling experiments, indicates that essentially all of the styrene oxide that reacts with cleavage of the benzyl C-O bond yields glycol with inversion of stereochemistry at the benzyl carbon.A mechanism involving addition of neutral water concerted with benzyl C-O bond breaking is proposed for this reaction.The glycol product from the acid-catalyzed reaction was determined to be the result of 67percent inversion and 33percent retention at the benzyl carbon.This result, which agrees with one previous publication and contradicts that of another, reflects the stereochemistry of addition of solvent to the benzyl carbon.Consistent with a recent report that 18O-hydroxide attacks the α- and β-carbons of styrene oxide at almost equal rates, styrene glycol from the reaction of chiral styrene oxide with sodium hydroxide was found to be, within experimental error, completely racemic.

-

Jensen,Kiskis

, p. 5825,5826 (1975)

-

Highly enantioselective conversion of racemic 1-phenyl-1,2-ethanediol by stereoinversion involving a novel cofactor-dependent oxidoreduction system of Candida parapsilosis CCTCC M203011

Nie, Yao,Xu, Yan,Mu, Xiao Qing

, p. 246 - 251 (2004)

An economical and convenient biocatalytic process was developed for the preparation of (S)-1-phenyl-1,2-ethanediol (PED), which is a valuable chiral building block for pharmaceuticals and liquid crystals, by stereoselective microbial conversion from the corresponding racemate. As a result of screening bacteria, yeasts, and molds, the enantioselective conversion of racemic PED by Candida parapsilosis CCTCC M203011 was found to be the most efficient process to produce (S)-PED with high optical purity of 98% ee and yield of 92%. By detecting the intermediate produced in the reaction by GC-MS, it was suggested that (S)-enantiomer was produced from the intermediate identified as β-hydroxyacetophenone by asymmetric reduction after stereoselective oxidation of (R)-enantiomer to β-hydroxyacetophenone. After investigating the cofactor requirement and stereospecificity of the reaction catalyzed by the cell-free extract from C. parapsilosis CCTCC M203011, it was found that the stereoselective conversion involved the oxidation of (R)-PED to the intermediate with NADP+ as the cofactor and the reduction reaction that formed the product used NADH as the cofactor, which was catalyzed by a novel cofactor-dependent oxidoreduction system. The NADP+-dependent (R)-specific alcohol dehydrogenase involved in stereoinversion was purified from C. parapsilosis CCTCC M203011, which has a relative molecular mass of 45kD.

Rhodium catalysed enantioselective hydroboration of alkenylboronic esters with catecholborane

Wiesauer, Christian,Weissensteiner, Walter

, p. 5 - 8 (1996)

Alkenylboronic esters such as (E)-2-(2-phenylethenyl)-1,3,2-dioxaborolane were subjected to catalytic hydroboration with catecholborane and with use of neutral and cationic rhodium complexes modified by various diphosphine ligands. The resulting 1,2-diboryl intermediate was oxidised with alkaline hydrogen peroxide to give the corresponding 1,2-diol with enantioselectivities up to 79% e.e.

Microbiological Transformations. 28. Enantiocomplementary Epoxide Hydrolyses as a Preparative Access to Both Enantiomers of Styrene Oxide

Pedragosa-Moreau, S.,Archelas, A.,Furstoss, R.

, p. 5533 - 5536 (1993)

-

Asymmetric dihydroxylation with silica-anchored alkaloids

Bolm, Carsten,Maischak, Astrid,Gerlach, Arne

, p. 2353 - 2354 (1997)

Diols with excellent enantiomeric excesses are obtained from unfunctionalised alkenes in high yields by osmium-catalysed dihydroxylationsusingsilica-boundpyrimidineandpyrazino-pyridazine ligands.

Enantioselective hydrolysis of styrene oxide with the epoxide hydrolase of Sphingomonas sp. HXN-200

Liu, Zeya,Michel, Johannes,Wang, Zunsheng,Witholt, Bernard,Li, Zhi

, p. 47 - 52 (2006)

The soluble bacterial epoxide hydrolase (EH) from Sphingomonas sp. HXN-200 catalyzed the enantioselective hydrolysis of racemic styrene oxide to give (S)-styrene oxide with an enantiomeric ratio (E) of 21-23 in aqueous buffer, better than any reported native EHs. The ring opening of the styrene oxide with this EH was only at the terminal position for the (S)-enantiomer and at the terminal and benzylic position in an 87:13 ratio for the (R)-enantiomer. Enzymatic hydrolysis of the styrene oxide in a two-liquid phase system significantly reduced autohydrolysis, thus improving the E to 26-29. Hydrolysis of 160 mM styrene oxide with cell-free extract (CFE) of Sphingomonas sp. HXN-200 (10 mg protein/mL) in aqueous buffer and n-hexane (1:1) for 30.7 h afforded 39.2% (62.7 mM) of (S)-styrene oxide in >99.9% ee. The lyophilized CFE was proven to be stable, while the rehydrated lyophilized CFE powder was successfully used for the hydrolysis of 320 mM styrene oxide in the two-liquid phase system, yielding 40.2% (128.6 mM) of (S)-styrene oxide in >99.9% ee after 13.8 h. No inhibitory effect of the diol product on the hydrolysis was observed when the diol concentration was lower than 476 mM, suggesting a straightforward process for the hydrolysis of up to 1 M styrene oxide.

Using deep eutectic solvents to improve the biocatalytic reduction of 2-hydroxyacetophenone to (R)-1-phenyl-1,2-ethanediol by Kurthia gibsonii SC0312

Peng, Fei,Chen, Qing-Sheng,Li, Fang-Zhou,Ou, Xiao-Yang,Zong, Min-Hua,Lou, Wen-Yong

, (2020)

The effects of five deep eutectic solvents (DESs) on the production of (R)-1-phenyl-1,2-ethanediol from 2-hydroxyacetophenone catalyzed by Kurthia gibsonii SC0312 were investigated in this study. Of these, choline chloride/1,4-butanediol (ChCl/Bd) showed excellent biocompatibility and suitably increased the cell membrane permeability while having a little impact on the structure of DNA. Indeed, ChCl/Bd at the concentration of 2 % increased the catalytic rate of the cells by 22 %. The other DESs did not stimulate the catalytic capacity of the cells, despite some increases in the cell membrane permeability. Additionally, the conformation of DNA was visibly changed when adding the other examined DESs except for choline chloride/triethylene glycol. The DESs modified the fatty acid composition of cellular membrane, decreased the relative amount of iso-C14:0 and increased the relative amount of normal C15:0. Meanwhile, the DESs were able to improve the relative ratio of normal fatty acids to branched fatty acids. Finally, a highly efficient reduction of 80 mM 2-hydroxyacetophenone by K. gibsonii SC0312 in the ChCl/Bd-containing system was established, affording (R)-1-phenyl-1,2-ethanediol in 80 % yield and optical purity >99 % at 30 mg/mL wet cells. This work offers a promising approach for the preparation of (R)-1-phenyl-1,2-ethanediol from 2-hydroxyacetophenone using K. gibsonii SC0312.

Stereoselective 1,2-additions of α-alkoxymethyllithiums to aldehydes

Smyj, Robert P.,Chong, J. Michael

, p. 2903 - 2906 (2001)

(equation presented) A chiral derivative of tributylstannymethanol, readily prepared from L-valine, undergoes Sn-Li exhange to provide an α-alkoxyorganolithium that adds to aldehydes with up to 91:9 dr. The diastereoselectivity depends on the solvent and alkyllithium used for transmetalation. Treatment of adducts with acid allowed recovery of the chiral auxiliary and diol with complete stereochemical integrity.

Resolution of 1,2-diols by enzyme-catalyzed oxidation with anodic, mediated cofactor regeneration in the extractive membrane reactor: Gaining insight by adaptive simulation

Degenring, Daniela,Schroeder, Iris,Wandrey, Christian,Liese, Andreas,Greiner, Lasse

, p. 213 - 218 (2004)

Oxidative racemic resolution of 1,2-diols is a method for the synthesis of enantiopure diols not easily accessed by reduction. The constraints generally found for oxidation to hydroxy ketones can be overcome by coupling various techniques. To circumvent product inhibition, a membrane reactor with solvent extraction of the lipophilic product was chosen. For the oxidative regeneration of NAD+ from NADH anodic oxidation mediated by ABTS was used. The kinetic characteristics of the system were determined independently for each significant system step. However, it proved difficult to simulate the coupled process completely with the kinetic data obtained independently, as true reaction conditions are not covered by kinetic experiments. A mixed approach using a system of ordinary differential equations corrected with data from the process (e.g. enzyme activity) leads to a satisfactory description. This model was applied as a starting point for identifying the relevant process parameters.

Directed Evolution of Alcohol Dehydrogenase for Improved Stereoselective Redox Transformations of 1-Phenylethane-1,2-diol and Its Corresponding Acyloin

Hamnevik, Emil,Maurer, Dirk,Enugala, Thilak Reddy,Chu, Thao,L?fgren, Robin,Dobritzsch, Doreen,Widersten, Mikael

, p. 1059 - 1062 (2018)

Laboratory evolution of alcohol dehydrogenase produced enzyme variants with improved turnover numbers with a vicinal 1,2-diol and its corresponding hydroxyketone. Crystal structure and transient kinetics analysis aids in rationalizing the new functions of these variants.

In defense of the catalytic asymmetric cis dihydroxylation of olefins utilizing insoluble polymeric ligands [6]

Salvadori,Pini,Petri

, p. 6929 - 6930 (1997)

-

Tridentate nitrogen phosphine ligand containing arylamine NH as well as preparation method and application thereof

-

Paragraph 0117-0120, (2021/06/26)

The invention discloses a tridentate nitrogen phosphine ligand containing arylamine NH as well as a preparation method and application thereof, and belongs to the technical field of organic synthesis. The tridentate nitrogen phosphine ligand disclosed by the invention is the first case of tridentate nitrogen phosphine ligand containing not only a quinoline amine structure but also chiral ferrocene at present, a noble metal complex of the type of ligand shows good selectivity and extremely high catalytic activity in an asymmetric hydrogenation reaction, meanwhile, a cheap metal complex of the ligand can also show good selectivity and catalytic activity in the asymmetric hydrogenation reaction, and is very easy to modify in the aspects of electronic effect and space structure, so that the ligand has huge potential application value. A catalyst formed by the ligand and a transition metal complex can be used for catalyzing various reactions, can be used for synthesizing various drugs, and has important industrial application value.

An easy and low-cost method of embedding chiral molecules in metal-organic frameworks for enantioseparation

Cao, Rong,Fang, Zhi-Bin,Hu, Xiao-Jing,Huang, Ge,Liu, Tian-Fu,Zhang, Shuo

supporting information, p. 7459 - 7462 (2020/07/15)

A facile method, post-synthetic exchange of modulators (PSEm), has been demonstrated here to prepare chiral metal-organic frameworks for enantioseparation. Based on this method, three chiral porous Zr-based metal-organic frameworks have been prepared through exchanging the coordinated modulators on metal clusters of MOFs with commercially available chiral carboxylic acid molecules. In addition, the obtained materials show enantioselectivity toward three different enantiomers, which presents a proof of concept for the design of MOF materials for enantioseparation by an easy and low-cost method. This journal is

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