1-O-ALLYL-2-DEOXY-4,6-O-ISOPROPYLIDENE-2-(TRIFLUOROACETAMIDO)-ALPHA-D-GLUCO-PYRANOSIDE

Base Information

• Chemical Name: 1-O-ALLYL-2-DEOXY-4,6-O-ISOPROPYLIDENE-2-(TRIFLUOROACETAMIDO)-ALPHA-D-GLUCO-PYRANOSIDE
• CAS No.: 139629-59-7
• Molecular Formula: C14H20 F3 N O6
• Molecular Weight: 355.311
• Hs Code.: 29389090
• Mol file: 139629-59-7.mol

Synonyms:a-D-Glucopyranoside, 2-propenyl2-deoxy-4,6-O-(1-methylethylidene)-2-[(trifluoroacetyl)amino]- (9CI);Pyrano[3,2-d]-1,3-dioxin, a-D-glucopyranoside deriv.

Chemical Property of 1-O-ALLYL-2-DEOXY-4,6-O-ISOPROPYLIDENE-2-(TRIFLUOROACETAMIDO)-ALPHA-D-GLUCO-PYRANOSIDE

Chemical Property:

• Melting Point: 94-96 °C(lit.)
• PSA: 86.25000
• LogP: 0.86430

Purity/Quality:

99.0%min ^*data from raw suppliers

Allyl 2-deoxy-4,6-O-isopropylidene-2-(trifluoroacetamido)-a-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-O-ALLYL-2-DEOXY-4,6-O-ISOPROPYLIDENE-2-(TRIFLUOROACETAMIDO)-ALPHA-D-GLUCO-PYRANOSIDE

There total 3 articles about 1-O-ALLYL-2-DEOXY-4,6-O-ISOPROPYLIDENE-2-(TRIFLUOROACETAMIDO)-ALPHA-D-GLUCO-PYRANOSIDE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 28.7%

allyl 2-deoxy-2-trifluoroacetylamino-D-glucopyranoside (132760-30-6) + 2,2-dimethoxy-propane (77-76-9) → allyl 2-deoxy-4,6-O-isopropylidene-2-trifluoroacetylamino-β-D-glucopyranoside (135226-04-9) + 1-O-allyl-2-deoxy-4,6-isopropylidene-2-(trifluoroacetamido)-α-D-glucopyranoside (139629-59-7)

Guidance literature:

With pyridinium p-toluenesulfonate; In N,N-dimethyl-formamide; for 3h; Ambient temperature;

DOI:10.1016/0008-6215(91)89006-2

Reference yield:

2-trifluoroacetamido-2-deoxy-α,β-D-glucopyranose (667462-08-0) → 1-O-allyl-2-deoxy-4,6-isopropylidene-2-(trifluoroacetamido)-α-D-glucopyranoside (139629-59-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 2percent HCl / 0.5 h / Heating

2: 28.7 percent / pyridinium p-toluenesulfonate / dimethylformamide / 3 h / Ambient temperature

With hydrogenchloride; pyridinium p-toluenesulfonate; In N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(91)89006-2

Reference yield:

D-(+)-glucosamine hydrochloride (66-84-2) → 1-O-allyl-2-deoxy-4,6-isopropylidene-2-(trifluoroacetamido)-α-D-glucopyranoside (139629-59-7)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / methanol / Ambient temperature

2: 2percent HCl / 0.5 h / Heating

3: 28.7 percent / pyridinium p-toluenesulfonate / dimethylformamide / 3 h / Ambient temperature

With hydrogenchloride; pyridinium p-toluenesulfonate; triethylamine; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(91)89006-2

upstream raw materials:

allyl 2-deoxy-2-trifluoroacetylamino-D-glucopyranoside

2,2-dimethoxy-propane

2-trifluoroacetamido-2-deoxy-α,β-D-glucopyranose

D-(+)-glucosamine hydrochloride

Downstream raw materials:

allyl 2-<(2R,3S)-3-(benzyloxycarbonyloxy-2-fluorotetradecanoyl)amino>-2-deoxy-3-O-<(3R)-3-tetradecanoyloxytetradecanoyl>-α-D-glucopyranoside

allyl 2-<(2S,3R)-3-(benzyloxycarbonyloxy-2-fluorotetradecanoyl)amino>-2-deoxy-3-O-<(3R)-3-tetradecanoyloxytetradecanoyl>-α-D-glucopyranoside

allyl 2-<(2R,3S)-3-(benzyloxycarbonyloxy-2-fluorotetradecanoyl)amino>-2-deoxy-4,6-O-isopropylidene-3-O-<(3R)-3-tetradecanoyloxytetradecanoyl>-α-D-glucopyranoside

allyl 2-<(2S,3R)-3-(benzyloxycarbonyloxy-2-fluorotetradecanoyl)amino>-2-deoxy-4,6-O-isopropylidene-3-O-<(3R)-3-tetradecanoyloxytetradecanoyl>-α-D-glucopyranoside

Refernces