138319-97-8

Basic information

• Product Name: 3-<(tert-butoxycarbonyl)amino>-4-O-(tert-butyldiphenylsilyl)-3-deoxy-2,3-N,O-isopropylidene-L-threose
• CAS NO: 138319-97-8
• Molecular Weight: 497.707
• Mol File: 138319-97-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 3-<(tert-butoxycarbonyl)amino>-4-O-(tert-butyldiphenylsilyl)-3-deoxy-2,3-N,O-isopropylidene-L-threose(CAS DataBase Reference)
• NIST Chemistry Reference: 3-<(tert-butoxycarbonyl)amino>-4-O-(tert-butyldiphenylsilyl)-3-deoxy-2,3-N,O-isopropylidene-L-threose(138319-97-8)
• EPA Substance Registry System: 3-<(tert-butoxycarbonyl)amino>-4-O-(tert-butyldiphenylsilyl)-3-deoxy-2,3-N,O-isopropylidene-L-threose(138319-97-8)

Safety Data

• Hazardous Substances Data: 138319-97-8(Hazardous Substances Data)

Upstream product

• 176967-05-8 (4R,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 176967-02-5 (2S,3R)-3-amino-4-tert-butyldiphenylsilyloxy-butane-1,2-diol 
• 138319-96-7 (4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-thiazol-2-yl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 138319-96-7 (1S,2R)-2-<(tert-Butoxycarbonyl)amino>-3-<(tert-butyldiphenylsilyl)oxy>-1-hydroxy-2-N,1-O-isopropylidene-1-(1,3-thiazol-2-yl)propane 
• 138319-92-3 (1S,2R)-2-<(tert-Butoxycarbonyl)amino>-3-<(tert-butyldiphenylsilyl)oxy>-1-(1,3-thiazol-2-yl)-1-propanol 
• 115822-50-9 (R)-2-<(tert-Butoxycarbonyl)amino>-3-hydroxy-2-N,3-O-isopropylidene-1-(1,3-thiazol-2-yl)-1-propanone 
• 145532-48-5 (1S,2R)-2-<(tert-Butoxycarbonyl)amino>-3-hydroxy-2-N,3-O-isopropylidene-1-(1,3-thiazol-2-yl)-1-propanol 
• 138319-91-2 ((1R,2S)-2-Hydroxy-1-hydroxymethyl-2-thiazol-2-yl-ethyl)-carbamic acid tert-butyl ester 
• 108149-60-6 methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate 
• 176967-04-7 2-Nitro-benzoic acid (2S,3R)-3-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-butyl ester 
• 177186-43-5 (2S,3R)-3-N-tert-butoxycarbonylamino-4-tert-butyldiphenylsilyloxy-butane-1,2-diol 
• 177186-42-4 (2S,3R)-3-amino-4-tert-butyldiphenylsilyloxy-1,2-isopropylidenedioxy-butane 

Downstream Products

• 138319-93-4 (4R,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-((E)-2-thiazol-2-yl-vinyl)-oxazolidine-3-carboxylic acid tert-butyl ester 
• 138319-93-4 (4S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-((E)-2-thiazol-2-yl-vinyl)-oxazolidine-3-carboxylic acid tert-butyl ester 
• 177186-44-6 (4R,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-((Z)-pentadec-1-enyl)-oxazolidine-3-carboxylic acid tert-butyl ester 
• 138346-55-1 (4R,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-((1R,2R)-1,2-dihydroxy-2-thiazol-2-yl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 138346-55-1 (4R,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-((1S,2S)-1,2-dihydroxy-2-thiazol-2-yl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 138319-94-5 (4R,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-((4S,5R)-2,2-dimethyl-5-thiazol-2-yl-[1,3]dioxolan-4-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 138346-55-1 (4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-((1R,2R)-1,2-dihydroxy-2-thiazol-2-yl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 138383-64-9 (4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-((1S,2S)-1,2-dihydroxy-2-thiazol-2-yl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 138319-94-5 (4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-((4R,5S)-2,2-dimethyl-5-thiazol-2-yl-[1,3]dioxolan-4-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 172213-39-7 (4R,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-((E)-pentadec-1-enyl)-oxazolidine-3-carboxylic acid tert-butyl ester 
• 192129-68-3 (4R,5R)-5-((S)-3-Benzyloxycarbonylamino-1-methyl-propyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 192129-55-8 (4R,5R)-5-((R)-3-Benzyloxycarbonylamino-1-methyl-propyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 192129-54-7 (4R,5R)-5-((S)-3-Azido-1-methyl-propyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 192129-53-6 (4R,5R)-5-((R)-3-Azido-1-methyl-propyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 

Relevant articles and documents

Formal synthesis of an unusual amino acid component of cyclosporin, involving stereocontrolled nucleophilic 1,4-addition

A syn-(2R)-amino-1,3,4-butanetriol derivative, readily available from D-isoascorbic acid, was utilized for the synthesis of MeBmt found in the immunosuppressive undecacyclopeptide cyclosporin. This new strategy involves diastereoselective nucleophilic 1,4-addition of lithium dimethylcuprate to a chiral α,β-unsaturated aldehyde, and elaboration of the terminal double bond, by Takai or Wittig method for the MeBmt or its 6Z-isomer, respectively.

Synthesis of (2S,3R)-3-amino-2-hydroxydecanoic acid and (3R,4R)-3-amino-4-hydroxyazepane from D-isoascorbic acid

Taking advantage of the high functionally of an enantiopure protected syn-2R-amino-1,3,4-triol derivative, easily available on a multigram scale from D-isoascorbic acid, several biologically active compounds have been synthesized such as the (2S,3R)-3-amino-2-hydroxydecanoic acid (AHDA), the N-terminal moiety of microginin, and the (3R,4R)-3-amino-4-hydroxyazepane, the ophiocordin and balanol core structure.

Efficacious Modification of the Procedure for the Aldehyde Release from 2-Substituted Thiazoles

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