18981-63-0

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

• 32385-07-2 methyl 3-acetamido-2,3,6-trideoxy-α-L-lyxo-hexopyranoside 
• 108-24-7 acetic anhydride 
• 32385-06-1 (2S,3S,4S)-4-amino-6-methoxy-2-methyltetrahydro-2H-pyran-3-ol hydrochloride 
• 189316-37-8 N-[(S)-1-((2R,4S,5S)-5-Methyl-2-phenyl-[1,3]dioxolan-4-yl)-3-oxo-propyl]-acetamide 
• 91366-56-2 Methyl 2-iodo-3-amino-2,3,6-trideoxy-α-L-galactopyranoside hydrochloride 
• 18977-92-9 methyl α-DL-daunosaminide 
• 84851-97-8 (3S,5S)-2-Benzyl-5-ethoxy-3-((4S,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-isoxazolidine 
• 75124-22-0 Methyl-2,3,6-tridesoxy-3-(p-tolylsulfonylamino)-α-L-lyxo-hexopyranosid 
• 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 

Relevant academic research and scientific papers

Stereocontrolled routes to cis-hydroxyamino sugars, Part VII: Synthesis of daunosamine and ristosamine.

The nitrogen of an allylic amine can serve as the fulcrum for stereocontrolled delivery of oxygen to an adjacent trigonal site, and cis-hydroxyamino sugars can thus be prepared. Methods for achieving the complementary procedure, namely, control of the delivery of nitrogen to an adjacent site by an allylic oxygen, are described. For example, treatment of methyl 2,3,6-trideoxy-alpha-L-erythro-hex-2-enopyranoside with trichloroacetonitrile gave an imidate ester which reacted with iodonium dicollidine perchlorate to give 2-trichloromethyl-(methyl 2,3,4,6-tetradeoxy-2-iodo-alpha-L-altropyranosido)-[3,4-d]-2-oxazo line. Exhaustive reductive dehalogenation of this product followed by hydrolysis led to methyl N-acetyl-alpha-L-ristosaminide. An analogous series of reactions was used to prepare the corresponding daunosaminide.

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).

The total synthesis of L-daunosamine

N,O-Dibenzyl-N-tert-butoxycarbonyl-L-homoserinal (7), obtained from L-aspartic acid, reacts with vinylmagnesium chloride to afford with high stereoselectivity compound 6 which is subsequently transformed into the derivative of L

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

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.