458531-56-1

Basic information

• Product Name: Carbamic acid, [(1S)-2-hydroxy-1-methyl-3-butenyl]-, 1,1-dimethylethyl ester
• Synonyms: Carbamic acid, [(1S)-2-hydroxy-1-methyl-3-butenyl]-, 1,1-dimethylethyl ester
• CAS NO: 458531-56-1
• Molecular Formula: C₁₀H₁₉NO₃
• Molecular Weight: 201.26276
• Product Categories: N-BOC
• Mol File: 458531-56-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Carbamic acid, [(1S)-2-hydroxy-1-methyl-3-butenyl]-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(1S)-2-hydroxy-1-methyl-3-butenyl]-, 1,1-dimethylethyl ester(458531-56-1)
• EPA Substance Registry System: Carbamic acid, [(1S)-2-hydroxy-1-methyl-3-butenyl]-, 1,1-dimethylethyl ester(458531-56-1)

Safety Data

• Hazardous Substances Data: 458531-56-1(Hazardous Substances Data)

Upstream product

• 1826-67-1 vinyl magnesium bromide 
• 79069-13-9 (S)-2-t-butoxycarbonylaminopropan-1-ol 
• 28875-17-4 (S)-N-(tert-butoxycarbonyl)alanine methyl ester 
• 3536-96-7 vinylmagnesium chloride 
• 79069-50-4 Boc-Ala-H 

Downstream Products

• 1335287-06-3 (S)-2-[(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyloxycarbonyl]-1-methylethyl (2E,4R,5S)-5-{N-acryloyl-(E)-[2-methyl-3-(2-methyl-4-thiazolyl)allyl]amino}-4-(2-methoxyethoxy)methoxy-2-hexenoate 
• 1335287-01-8 (S)-2-[(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyloxycarbonyl]-1-methylethyl (2E,4R,5S)-5-(N-acryloyl-N-(4-methyl-2-thiazolyl)methylamino)-4-(2-methoxyethoxy)methoxy-2-hexenoate 
• 1335286-96-8 (S)-2-[(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyloxycarbonyl]-1-methylethyl (2E,4R,5S)-5-(N-acryloyl-N-(2-methyl-4-thiazolyl)methylamino)-4-(2-methoxyethoxy)methoxy-2-hexenoate 
• 1335286-91-3 (S)-2-[(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyloxycarbonyl]-1-methylethyl (2E,4R,5S)-5-(N-acryloyl-N-phenethylamino)-4-(2-methoxyethoxy)methoxy-2-hexenoate 
• 1335286-86-6 (S)-2-[(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyloxycarbonyl]-1-methylethyl (2E,4R,5S)-5-(N-acryloyl-N-benzylamino)-4-(2-methoxyethoxy)methoxy-2-hexenoate 
• 1335286-64-0 (1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyl (2E,4R,5S)-5-[(S)-3-acryloyloxybutyryl]amino-4-(2-methoxyethoxy)methoxy-2-hexenoate 
• 1335286-63-9 (1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyl (2E,4R,5S)-5-[(S)-3-hydoxybutyryl]amino-4-(2-methoxyethoxy)methoxy-2-hexenoate 
• 1335287-18-7 C₂₃H₂₅NO₇ 
• 1335287-17-6 C₂₃H₂₉NO₇ 
• 1335286-74-2 (3S,6E,8R,9S,12E,14R,15S)-16-benzyl-14-hydroxy-8-(2-methoxyethoxy)methoxy-3,9,15-trimethyl-16-aza-4,10-dioxa-6,12-cyclohexadecadiene-1,5,11-trione 
• 1335286-73-1 (S)-3-{N-benzyl-N-[(1R,2S)-2-hydroxy-1-methylbutenyl]amino}-1-methyl-3-oxo-propyl (2E,4R,5S)-5-acryloyloxy-4-(2-methoxyethoxy)methoxy-2-hexenoate 
• 1335286-72-0 (S)-3-{N-benzyl-N-[(1R,2S)-2-tert-butyldiphenylsilyloxy-1-methylbutenyl]amino}-1-methyl-3-oxo-propyl (2E,4R,5S)-5-acryloyloxy-4-(2-methoxyethoxy)methoxy-2-hexenoate 
• 1335286-71-9 (S)-3-{N-benzyl-N-[(1R,2S)-2-tert-butyldiphenylsilyloxy-1-methylbutenyl]amino}-1-methyl-3-oxo-propyl (2E,4R,5S)-5-hydroxy-4-(2-methoxyethoxy)methoxy-2-hexenoate 
• 1335286-70-8 (S)-3-{N-benzyl-N-[(1R,2S)-2-tert-butyldiphenylsilyloxy-1-methylbutenyl]amino}-1-methyl-3-oxo-propyl (2E,4R,5S)-5-tert-butyldiphenylsilyloxy-4-(2-methoxyethoxy)methoxy-2-hexenoate 

Relevant articles and documents

Concise total synthesis of (+)-carpamic acid

We report herein an efficient enantioselective synthesis of (+)-carpamic acid, with nine steps as the longest linear sequence, the key strategy being based on a novel sequence of a cross-metathesis (CM) reaction and a subsequent cyclizing reductive amination to form the piperidine ring.

Design and synthesis of sulfur based inhibitors of matrix metalloproteinase-1.

Fibroblast collagenase (MMP-1), a member of the matrix metalloproteinases family, is believed to be a pathogenesis of arthritis, by cleaving triple-helical type II collagen in cartilage. From the similarity of the active site zinc binding mode with hydroxamate, we designed and synthesized alpha-mercaptocarbonyl possessing compounds (3-5), which incorporated various peptide sequences as enzyme recognition sites. The P4-P1 peptide incorporating compound (3) exhibited as potent inhibition as the hydroxamate (1) and the carboxylate (2) type inhibitors, with an IC50 of 10(-6) M order against MMP-1. But the inhibitor (3) related compounds (6-8) displayed decreased or no inhibitory potencies. These results suggest that the existence of both the carbonyl and thiol groups might be critical for the inhibition, and the distance between the two functional groups is important for inhibitory potency. For Pn' peptide incorporating compounds (4a-k), except for 4h and 4k, all compounds showed IC50 values under sub-nanomolar. Among them, for potent inhibition, Leu was better than Phe and Val as the P1' amino acid, and the P2' position amino acid was necessary, and preferentially Phe. Insertion of the Pn peptide into 4d or 4k, giving compounds 5a-c, did not increase the activities of 4d and 4k. Substitution of the mercapto group with other functional groups lost the activity of compound 4a. The stereochemical preference at the thiol-attached position was also determined by preparation of both isomers of 4a. It was found that the S configuration compound (36b) is approximately 100 times more potent than the corresponding R-isomer (36a).

Palladium-catalyzed formation and stereoselective isomerization of 5- vinyloxazolines. Application to the formal synthesis of (S,S)-4-amino-3- hydroxy-5-phenylpentanoic acid

Vinyloxazolidinones have been found to undergo Pd(0)-catalyzed ionization followed by loss of carbon dioxide and subsequent cyclization to form vinyloxazolines. The reaction occurred under mild conditions, and enhancement of diastereomeric ratios with chiral substrates was obtained. 4- Benzyl-5-vinyloxazoline prepared by this method has been utilized in the stereoselective synthesis of (S,S)-4-amino-3-hydroxy-5-phenylpentanoic acid (AHPPA).