Welcome to LookChem.com Sign In|Join Free

Cas Database

499140-12-4

499140-12-4

Identification

Synonyms:benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate

Post Buying Request Now
Entrust LookChem procurement to find high-quality suppliers faster

Safety information and MSDS

Supplier and reference price

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
  • Delivery
  • Purchase

Relevant articles and documentsAll total 1 Articles be found

A General and Expeditious One-Pot Synthesis of Sulfoxides in High Optical Purity from Norephedrine-Derived Sulfamidites

Ruano, Jose L. Garcia,Alemparte, Carlos,Aranda, M. Teresa,Zarzuelo, Maria M.

, p. 75 - 78 (2003)

A general and simple procedure for preparing any kind of enantiomerically enriched sulfoxide starting from norephedrine-derived N-benzyloxycarbonylsulfamidite 3a is reported. After one-pot reaction of 3a with RMgX, HBF4, and R'MgX, a variety of sulfoxides 6 are obtained in ee usually higher than 93% and isolated yields ranging between 50 and 78%. The obtained configuration is tunable by simply electing the order of the addition of the reagents.

Process route upstream and downstream products

Process route

(1R,2S)-1-phenyl-2-benzyloxycarbonylamino-1-propanol
104863-92-5

(1R,2S)-1-phenyl-2-benzyloxycarbonylamino-1-propanol

benzyl (2S,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxylate
499140-11-3

benzyl (2S,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxylate

benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate
499140-12-4

benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate

Conditions
Conditions Yield
With dmap; thionyl chloride; In dichloromethane; at -40 ℃;
62%
With dmap; thionyl chloride; In dichloromethane; at -40 ℃; for 0.25h;
57%
With 2,6-dimethylpyridine; thionyl chloride; In dichloromethane; at -40 ℃;
44%
With 2,6-dimethylpyridine; thionyl chloride; In dichloromethane; at -40 ℃; for 0.25h;
44%
(1R,2S)-norephedrine
492-41-1,58550-13-3,757124-50-8

(1R,2S)-norephedrine

benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate
499140-12-4

benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 4-(N,N-dimethylamino)pyridine / CH2Cl2 / 0.08 h / 0 °C
2: thionyl chloride; 2,6-lutidine / CH2Cl2 / 0.25 h / -40 °C
With 2,6-dimethylpyridine; dmap; thionyl chloride; In dichloromethane;
benzyl chloroformate
501-53-1,94274-21-2

benzyl chloroformate

benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate
499140-12-4

benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 4-(N,N-dimethylamino)pyridine / CH2Cl2 / 0.08 h / 0 °C
2: thionyl chloride; 2,6-lutidine / CH2Cl2 / 0.25 h / -40 °C
With 2,6-dimethylpyridine; dmap; thionyl chloride; In dichloromethane;
methylmagnesium bromide
75-16-1

methylmagnesium bromide

benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate
499140-12-4

benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate

dimethyl sulfoxide
67-68-5,8070-53-9

dimethyl sulfoxide

(1R,2S)-2-{[(benzyloxy)carbonyl]amino}-1-phenylpropyl (S)-methanesulfinate

(1R,2S)-2-{[(benzyloxy)carbonyl]amino}-1-phenylpropyl (S)-methanesulfinate

Conditions
Conditions Yield
In dichloromethane; at -78 ℃;
65%
methyllithium
917-54-4

methyllithium

benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate
499140-12-4

benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate

dimethyl sulfoxide
67-68-5,8070-53-9

dimethyl sulfoxide

(1R,2S)-2-{[(benzyloxy)carbonyl]amino}-1-phenylpropyl (S)-methanesulfinate

(1R,2S)-2-{[(benzyloxy)carbonyl]amino}-1-phenylpropyl (S)-methanesulfinate

Conditions
Conditions Yield
In tetrahydrofuran; at -78 ℃; Title compound not separated from byproducts.;
methylmagnesium bromide
75-16-1

methylmagnesium bromide

benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate
499140-12-4

benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate

(1R,2S)-1-phenyl-2-benzyloxycarbonylamino-1-propanol
104863-92-5

(1R,2S)-1-phenyl-2-benzyloxycarbonylamino-1-propanol

dimethyl sulfoxide
67-68-5,8070-53-9

dimethyl sulfoxide

(1R,2S)-2-{[(benzyloxy)carbonyl]amino}-1-phenylpropyl (S)-methanesulfinate

(1R,2S)-2-{[(benzyloxy)carbonyl]amino}-1-phenylpropyl (S)-methanesulfinate

Conditions
Conditions Yield
With (-)-menthyl p-toluenesulfinate;
ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate
499140-12-4

benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate

diethyl sulphide
70-29-1

diethyl sulphide

(1R,2S)-2-{[(benzyloxy)carbonyl]amino}-1-phenylpropyl (S)-ethanesulfinate

(1R,2S)-2-{[(benzyloxy)carbonyl]amino}-1-phenylpropyl (S)-ethanesulfinate

Conditions
Conditions Yield
In dichloromethane; at -78 ℃;
46%
phenylmagnesium bromide

phenylmagnesium bromide

benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate
499140-12-4

benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate

1,1'-sulfinylbisbenzene
945-51-7

1,1'-sulfinylbisbenzene

(1R,2S)-2-{[(benzyloxy)carbonyl]amino}-1-phenylpropyl (S)-benzenesulfinate
499140-17-9

(1R,2S)-2-{[(benzyloxy)carbonyl]amino}-1-phenylpropyl (S)-benzenesulfinate

Conditions
Conditions Yield
In dichloromethane; at -78 ℃;
74%
phenylmagnesium bromide

phenylmagnesium bromide

benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate
499140-12-4

benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate

(1R,2S)-1-phenyl-2-benzyloxycarbonylamino-1-propanol
104863-92-5

(1R,2S)-1-phenyl-2-benzyloxycarbonylamino-1-propanol

(-)-(S)<sub>S</sub>-phenyl vinyl sulfoxide
20451-53-0,88180-53-4,89299-86-5,89299-85-4

(-)-(S)S-phenyl vinyl sulfoxide

(+)-(R)<sub>S</sub>-phenyl vinyl sulfoxide
89299-86-5

(+)-(R)S-phenyl vinyl sulfoxide

Conditions
Conditions Yield
phenylmagnesium bromide; benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate; In dichloromethane; at -78 ℃;
With tetrafluoroboric acid; In dichloromethane; at -78 ℃; for 0.0833333h;
vinyl magnesium halide; In dichloromethane; at -78 ℃; Further stages. Title compound not separated from byproducts.;
methylmagnesium bromide
75-16-1

methylmagnesium bromide

phenylmagnesium bromide

phenylmagnesium bromide

benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate
499140-12-4

benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate

(R)-methyl phenyl sulfoxide
4850-71-9

(R)-methyl phenyl sulfoxide

(1R,2S)-1-phenyl-2-benzyloxycarbonylamino-1-propanol
104863-92-5

(1R,2S)-1-phenyl-2-benzyloxycarbonylamino-1-propanol

Conditions
Conditions Yield
phenylmagnesium bromide; benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate; In dichloromethane; at -78 ℃;
With tetrafluoroboric acid; In diethyl ether; dichloromethane; at -78 ℃; for 0.0833333h;
methylmagnesium bromide; In dichloromethane; at -78 ℃; Further stages. Title compound not separated from byproducts.;

Global suppliers and manufacturers

Global( 0) Suppliers
  • Company Name
  • Business Type
  • Contact Tel
  • Emails
  • Main Products
  • Country
close
Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 499140-12-4
Post Buying Request Now
close
Remarks: The blank with*must be completed