2-DEOXY-2-PHTHALIMIDO-3,4,6-TRI-O-ACETYL-ALPHA-D-GLUCOPYRANOSYL FLUORIDE

Base Information

• Chemical Name: 2-DEOXY-2-PHTHALIMIDO-3,4,6-TRI-O-ACETYL-ALPHA-D-GLUCOPYRANOSYL FLUORIDE
• CAS No.: 147157-97-9
• Molecular Formula: C₂₀H₂₀FNO₉
• Molecular Weight: 437.379
• Hs Code.: 29349990
• Mol file: 147157-97-9.mol

Synonyms:2-DEOXY-2-PHTHALIMIDO-3,4,6-TRI-O-ACETYL-ALPHA-D-GLUCOPYRANOSYL FLUORIDE;2-deoxy-2-phthalimido-3,4,6-tri-O-*acetyl-A-D-;2-deoxy-2-phthalimido-3,4,6-tri-o-acetyl-α-d-glucopyranosyl fluoride;3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-a-D-glucopyranosylfluoride;2-deoxy-2-phthalimidotriacetyl-D-glucopyranosyl fluoride

Chemical Property of 2-DEOXY-2-PHTHALIMIDO-3,4,6-TRI-O-ACETYL-ALPHA-D-GLUCOPYRANOSYL FLUORIDE

Chemical Property:

• Refractive Index: 1.563
• PSA: 125.51000
• LogP: 0.71000

Purity/Quality:

99% ^*data from raw suppliers

3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-a-D-glucopyranosyl fluoride ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-DEOXY-2-PHTHALIMIDO-3,4,6-TRI-O-ACETYL-ALPHA-D-GLUCOPYRANOSYL FLUORIDE

There total 10 articles about 2-DEOXY-2-PHTHALIMIDO-3,4,6-TRI-O-ACETYL-ALPHA-D-GLUCOPYRANOSYL FLUORIDE 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: 96.0%

phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (79528-49-7) → 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride (130539-42-3,147157-97-9,177966-56-2)

Guidance literature:

With IF₅-pyridine-HF; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.carres.2015.08.005

Reference yield: 80.0%

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose (72858-55-0,90405-21-3,90405-42-8,124362-60-3,144221-86-3) → 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride (130539-42-3,147157-97-9,177966-56-2)

Guidance literature:

With diethylamino-sulfur trifluoride; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1021/ja0763605

Reference yield:

trifluoride + phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside (120498-97-7) → 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride (130539-42-3,147157-97-9,177966-56-2)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane;

upstream raw materials:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose

phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside

phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Downstream raw materials:

methyl 3,6-di-O-<2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl>-2,4-di-O-benzyl-α-D-mannopyranoside

benzyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->2)-O-[(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->6)]-3,4-di-O-benzyl-α-D-mannopyranoside

Refernces

• 1、 Stubbs, Keith A.,Scaffidi, Adrian,Debowski, Aleksandra W.,Mark, Brian L.,Stick, Robert V.,Vocadlo, David J.. "Synthesis and use of mechanism-based protein-profiling probes for retaining β-D-glucosaminidases facilitate identification of Pseudomonas aeruginosa NagZ". . p. 327 - 335. Retrieved 2008/10/09.
• 2、 Ikeshita, Shinji,Sakamoto, Akio,Nakahara, Yuko,Nakahara, Yoshiaki,Ogawa, Tomoya. "Synthesis of the root nodule-inducing factor NodRm-IV(C16:2,S) of rhizobium meliloti and related compounds". . p. 3123 - 3126. Retrieved 2007/10/02.