14086-88-5

Usage

Chemical Properties

White Solid

InChI:InChI=1/C8H15NO6/c1-3(11)9-5-6(12)4(2-10)15-8(14)7(5)13/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4?,5-,6+,7-,8+/m0/s1

Synthetic route

1,2:5,6-di-O-isopropylidene-3-O-(methylsulphonyl)-α-D-allofuranose (14728-80-4) + acetic anhydride (108-24-7) → 3-acetamido-3-deoxy-D-glucose (14086-88-5)

Conditions	Yield
(i) NaN3, DMF, (ii) H2, Pd-C, MeOH, (iii) /BRN= 385737/; Multistep reaction;

3-amino-3-deoxy-D-glucopyranose (19309-98-9) + acetic anhydride (108-24-7) → 3-acetamido-3-deoxy-D-glucose (14086-88-5)

Conditions	Yield
In methanol

3-azido-3-deoxy-D-glucopyranose (104875-44-7) → 3-acetamido-3-deoxy-D-glucose (14086-88-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / Pd(OH)2 2: methanol View Scheme

3-acetamido-3-deoxy-D-glucose (14086-88-5) + UDP-glucose → β,β-D-Gal-(1<->1)-D-Glc3NAc

Conditions	Yield
With α-lactalbumin In various solvent(s) at 30℃; for 30h; galactosyltransferase from bovine milk, UDP-glucose epimerase;	26%

Upstream product

• 19309-98-9 3-amino-3-deoxy-D-glucopyranose 
• 108-24-7 acetic anhydride 
• 19131-08-9 (3aR,5R,6S,6aR)-6-azido-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-tetrahydro-2H-furo[2,3-d][1,3]dioxole 
• 98301-94-1 3-acetamido-1,2,4,6-tetra-O-acetyl-3-deoxy-α,β-D-mannopyranose 
• 14728-80-4 1,2:5,6-di-O-isopropylidene-3-O-(methylsulphonyl)-α-D-allofuranose 
• 90706-19-7 Methyl 3-acetamido-3-deoxy-2-O-mesyl-α-D-glucopyranoside 
• 2484-80-2 Acetic acid (2S,3S,4S,5S,6R)-4-acetylamino-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl ester 
• 90706-18-6 methyl 3-acetamido-4,6-O-benzylidene-3-deoxy-2-O-mesyl-α-D-glucopyranoside 
• 72523-35-4 methyl 3-acetamido-2,4,6-tri-O-acetyl-3-deoxy-α-D-mannopyranoside 
• 17327-08-1 Methyl 3-acetamido-4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 14686-88-5 3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose 
• 26775-14-4 3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-gulofuranose 
• 14686-89-6 (1,2:5,6)-di-O-isopropylidene-D-gulose 

Downstream Products

• 72741-87-8 swainsonine 
• 90706-23-3 3-acetamido-2,4,5-tri-O-benzyl-3-deoxy-6-O-tosyl-D-mannose diethyl dithioacetal 
• 90706-28-8 swainsonine tribenzylate 
• 107741-02-6 (1S,2R,8R,8aR)-1,2,8-tris(benzyloxy)hexahydroindolizin-5(1H)-one 
• 90706-24-4 (S)-((2S,3S,4R)-1-Acetyl-3,4-bis-benzyloxy-pyrrolidin-2-yl)-benzyloxy-acetaldehyde 
• 90706-25-5 (2S,3S,4R)-1-acetyl-3,4-dibenzyloxy-2-<(1S)-1-benzyloxy-2,2-bis(ethylthio)-ethyl>pyrrolidine 
• 90706-22-2 3-acetamido-2,4,5-tri-O-benzyl-3-deoxy-D-mannose diethyl dithioacetal 
• 90706-27-7 (2R,3S,4R)-1-acetyl-3,4-dibenzyloxy-2-<(1R)-1-benzyloxy-3-ethoxycarbonylpropyl>pyrrolidine 
• 90706-21-1 3-acetamido-3-deoxy-6-O-triphenylmethyl-D-mannose diethyl dithioacetal 
• 90706-26-6 (E)-(R)-4-((2R,3S,4R)-1-Acetyl-3,4-bis-benzyloxy-pyrrolidin-2-yl)-4-benzyloxy-but-2-enoic acid ethyl ester 
• 90762-27-9 (2R,3S,4R)-1-acetyl-3,4-dibenzyloxy-2-<(1R,2Z)-1-benzyloxy-3-ethoxycarbonyl-2-propenyl>pyrrolidine 
• 90706-26-6 (2R,3S,4R)-1-acetyl-3,4-dibenzyloxy-2-<(1R,2E)-1-benzyloxy-3-ethoxycarbonyl-2-propenyl>pyrrolidine 

Relevant academic research and scientific papers

TOTAL SYNTHESIS OF (-)-SWAINSONINE, AN α-MANNOSIDASE INHIBITOR ISOLATED FROM SWAINSONA CANESCENS

The alkaloidal toxin, (-)-swainsonine: (1S,2R,8R,8aR)-1,2,8-trihydroxyoctahydroindolizine has been synthesized stereoselectively starting from methyl 3-acetamido-2,4,6-tri-O-acetyl-3-deoxy-α-D-mannopyranoside in a 15 steps rection.

A new Approach to 3-Acetylamino-3-desoxy-D-galactose

The synthesis of the title compound from 1,2:5,6-Di-O-isopropyliden-α-D-glucofuranose (1) via 1,2:5,6-Di-O-isopropyliden-α-D-gulofuranose (4) is reported.The key-step is the introduction of the azido function into 4 which is achieved by using Triphenylphosphane/Diethylazodicarboxylate/HN3. - Keywords: 3-Acetylamino-3-desoxy-D-galactose, syntheses of; TPP-DEAD-HN3, reaction with 1,2:5,6-Di-O-isopropyliden-α-D-gulofuranose