18981-63-0

Basic information

• Product Name: 1-O-Methyl-3-(acetylamino)-4-O-acetyl-2,3,6-trideoxy-α-L-lyxo-hexopyranose
• Synonyms: 1-O-Methyl-3-(acetylamino)-4-O-acetyl-2,3,6-trideoxy-α-L-lyxo-hexopyranose
• CAS NO: 18981-63-0
• Molecular Formula: C11H19NO5
• Molecular Weight: 245.27226
• Mol File: 18981-63-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 394.4°C at 760 mmHg
• Flash Point: 192.3°C
• Appearance: /
• Density: 1.14g/cm³
• Vapor Pressure: 1.98E-06mmHg at 25°C
• Refractive Index: 1.47
• CAS DataBase Reference: 1-O-Methyl-3-(acetylamino)-4-O-acetyl-2,3,6-trideoxy-α-L-lyxo-hexopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O-Methyl-3-(acetylamino)-4-O-acetyl-2,3,6-trideoxy-α-L-lyxo-hexopyranose(18981-63-0)
• EPA Substance Registry System: 1-O-Methyl-3-(acetylamino)-4-O-acetyl-2,3,6-trideoxy-α-L-lyxo-hexopyranose(18981-63-0)

Safety Data

• Hazardous Substances Data: 18981-63-0(Hazardous Substances Data)

Usage

Derivative of L-lyxose

A sugar molecule
A modified version of the sugar molecule L-lyxose, which is a naturally occurring hexose (six-carbon sugar).

Functional groups

Methyl, acetylamino, and acetyl groups

Methyl group

A -CH3 group that provides steric hindrance and electronic effects.

Acetylamino group

An -NHCOCH3 group that can participate in hydrogen bonding and nucleophilic reactions.

Acetyl group

A -COCH3 group that can undergo nucleophilic acyl substitution and influence the compound's reactivity.

Starting material in synthesis

Pharmaceutical and natural products
The compound is commonly used as a starting material in the synthesis of various pharmaceuticals and natural products due to its unique structure and properties.

Value in organic chemistry and drug development

Unique structure and properties
The compound's structure and properties make it valuable for use in organic chemistry research and the development of new drugs, as it can be modified and functionalized in various ways to create new molecules with desired biological activities.

InChI:InChI=1/C11H19NO5/c1-6-11(17-8(3)14)9(12-7(2)13)5-10(15-4)16-6/h6,9-11H,5H2,1-4H3,(H,12,13)

Upstream product

• 142545-29-7 4(S)-(N-Benzyl-N-tert-butyloxycarbonyl)amino-6-benzyloxy-2,3-(2S,3S)-isopropylidenedioxyhexane 
• 142545-23-1 4(S)-(N-Benzyl-N-tert-butoxycarbonyl)amino-6-benzyloxy-1,2-2(S)-epoxy-3(S)-hydroxyhexane 
• 142545-32-2 Benzyl-[(1S,2S,3S)-1-(2-benzyloxy-ethyl)-2,3-dihydroxy-butyl]-carbamic acid tert-butyl ester 
• 142545-24-2 4(S)-(N-Benzyl-N-tert-butoxycarbonyl)amino-6-benzyloxy-3(R)-hydroxyhexene-1 
• 142545-30-0 4(S)-(N-tert-Butyloxycarbonyl)amino-6-hydroxy-2,3-(2S,3S)-isopropylidenedioxyhexane 
• 142545-31-1 [(S)-3-Oxo-1-((4S,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-propyl]-carbamic acid tert-butyl ester 
• 108-24-7 acetic anhydride 
• 18977-92-9 (3S,4S)-4-Amino-6-methoxy-2-methyl-tetrahydro-pyran-3-ol 
• 83803-05-8 2,3,4,6-tetradeoxy-4',5'-dihydro-2-iodo-2'-trichloromethyl(methyl α-DL-altropyranosido)<3,4-d>oxazole 
• 83803-03-6 methyl 2,3,6-trideoxy-4-O-trichloroacetimidoyl-α-DL-threo-hex-2-enopyranoside 
• 83803-06-9 2,3,4,6-tetradeoxy-4',5'-dihydro-2'-trichloromethyl(methyl α-DL-lyxo-hexopyranosido)<3,4-d>oxazole 
• 33647-82-4 methyl 2,3,6-trideoxy-α-DL-glycero-hex-2-enopyranosid-4-ulose 
• 26922-36-1 methyl 2,3,6-trideoxy-α-DL-threo-hex-2-enopyranoside 
• 33647-67-5 1-(2,5-dimethoxy-2,5-dihydrofuran-2-yl)ethanol from 2-Acetylfuran 

Relevant articles and documents

Regio- and stereoselective synthesis of methyl α-L-daunosaminide hydrochloride

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Synthesis of L-daunosamine derivatives on the basis of the asymmetric dihydroxylation of 3-((E)-1-propenyl)-4,5-dihydroisoxazole

Methyl L-N,O-diacetyldaunosaminide was prepared from 3-nitro-4,5-dihydroisoxazole in 8.5% overall yield. A key step in the synthesis involved the AD reaction of (E)-3-(1-propenyl)-4,5-dihydroisoxazole (2b), affording the corresponding diol in 76% yield (92% ee). A second key step involved reductive cleavage of the dihydroisoxazole 4a and subsequent N-acetylation to afford separable diastereomeric γ-(acetylamino)alcohols 7a and 8a in 62% yield (72:28, 7a/8a). Swern oxidation of 7a and subsequent methanolysis followed by acetylation provided methyl L-N,O-diacetyldaunosaminide as an anomeric mixture. The AD reactions of chiral alkenyl dihydroisoxazole 16 with (DHQ)2-PHAL and (DHQD)2-PHAL afforded diastereomeric diol products, isolated as the acetates 18 and 19 (98:2 and 5:95 ratios, respectively, depending on the chiral auxiliary).

A DIHYDROISOXAZOLE-BASED ROUTE TO 2,3,6-TRIDEOXY-3-AMINOHEXOSE DERIVATIVES

Acosamine and ristosamine derivatives were prepared via stereoselective reductive cleavage reactions of a benzylidenated dihydroisoxazolyl diol; the diol was prepared from 3-nitro-4,5-dihydroisoxazole via sequential propynylation, Lindlar reduction, and c