54623-24-4

Basic information

• Product Name: METHYL-A-L-ACOSAMINE
• Synonyms: METHYL-A-L-ACOSAMINE;METHYL-L-ACOSAMINIDE;METHYL-L-ACOSAMINIDE HYDROCHLORIDE;ACOSAMINE METHYL GLYCOSIDE;ACOSAMINE METHYL GLYCOSIDE HYDROCHLORIDE;Methyl-L-Acosaminide, Acosamine Methyl Glycoside;Acosamine hydrochloride methyl glycoside;METHYL-ALPHA-L-ACOSAMINE
• CAS NO: 54623-24-4
• Molecular Formula: C₇H₁₅NO₃*ClH
• Molecular Weight: 197.66
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 54623-24-4.mol

Chemical Properties

• Melting Point: 130-132°C
• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: METHYL-A-L-ACOSAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL-A-L-ACOSAMINE(54623-24-4)
• EPA Substance Registry System: METHYL-A-L-ACOSAMINE(54623-24-4)

Safety Data

• Hazardous Substances Data: 54623-24-4(Hazardous Substances Data)

Usage

Chemical Properties

White Crystalline Solid

Upstream product

• 83803-05-8 2,3,4,6-tetradeoxy-4',5'-dihydro-2-iodo-2'-trichloromethyl(methyl α-DL-altropyranosido)<3,4-d>oxazole 
• 89128-75-6 methyl 3-amino-2,3,6-trideoxy-2-iodo-α-DL-galactopyranoside hydrochloride 
• 89128-75-6 methyl 3-amino-2,3,6-trideoxy-2-iodo-α-DL-altropyranoside hydrochloride 
• 184840-85-5 tert-Butyl (3S,αR)-(E)-3-[N-benzyl-N-(α-methylbenzyl)amino]hex-4-enoate 
• 178976-42-6 Methyl (3S,αR)-(E)-3-[N-benzyl-N-(α-methylbenzyl)amino]hex-4-enoate 
• 81838-85-9 tert-butyl (2E,4E)-2,4-hexadienoate 
• 689-89-4 (2E,4E)-methylhexa-2,4-dienoate 
• 110-44-1 sorbic Acid 
• 67-56-1 methanol 
• 1300575-48-7 C₁₁H₁₉NO₅ 
• 1300575-47-6 C₁₁H₁₉NO₅ 
• 83803-03-6 methyl 2,3,6-trideoxy-4-O-trichloroacetimidoyl-α-DL-erythro-hex-2-enopyranoside 
• 33647-67-5 1-(2,5-dimethoxy-2,5-dihydrofuran-2-yl)ethanol from 2-Acetylfuran 
• 1192-62-7 1-(2-furyl)-1-ethanone 

Relevant articles and documents

Concise and highly selective asymmetric synthesis of acosamine from sorbic acid

Diastereoselective conjugate addition of lithium (R)-N-benzyl-N-(α- methylbenzyl)amide to tert-butyl sorbate and subsequent chemo- and diastereoselective ammonium-directed olefinic oxidation of the resultant conjugate addition product {tert-butyl (3S,αR)-3-[N-benzyl-N-(α- methylbenzyl)amino]hex-4-ene} have been used as the key steps in a concise and highly selective asymmetric synthesis of the 2,3,6-trideoxy-3-aminohexose l-acosamine. This sequence of two chemical operations allows rapid assembly of the molecular architecture and facilitates the de novo asymmetric synthesis of methyl N,O-diacetyl-α-l-acosaminide in only 7 steps from commercially available sorbic acid in 15% overall yield.

SYNTHESIS OF (L)-DAUNOSAMINE AND RELATED AMINO SUGARS

1-(2-Furyl)ethanol (6) has been converted into methyl (+/-)-daunosaminide (1) and methyl (+/-)-ristosaminide (3) by use of an intramolecular cyclisation of a trichloroacetimidate group. (+/-)-Daunosamine (1) has been obtained more directly from the alcohol (10) by use of a modified Mitsunobu reaction; the scope of the latter reaction has been explored using cyclohex-2-en-1-ol as a model substrate.Asymmetric reduction of 2-acetylfuran (5) has given (S)-1-(2-furyl)ethanol (46) in good enantiomeric excess, thus providing a short route to the L-enantiomers of the amino sugars (1), (2), and (3) from a cheap, non-carbohydrate precursor.

A New Route to (+/-)-Daunosamine and Related Amino-sugars

1-(2-Furyl)ethanol has been converted into (+/-)-daunosamine by use of a modified Mitsunobu reaction.