2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl Fluoride

Base Information

• Chemical Name: 2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl Fluoride
• CAS No.: 89025-46-7
• Molecular Formula: C34H35 F O5
• Molecular Weight: 542.647
• Hs Code.: 29329990
• DSSTox Substance ID: DTXSID40454866
• Nikkaji Number: J370.567F
• Wikidata: Q82276649
• Mol file: 89025-46-7.mol

Synonyms:89025-46-7;2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl Fluoride;(2R,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-fluorotetrahydro-2H-pyran;(2R,3R,4S,5R,6R)-2-fluoro-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane;2,3,4,6-Tetra-O-benzyl-|A-D-glucopyranosyl Fluoride;SCHEMBL2124878;DTXSID40454866;MFCD03701104;AKOS015888992;HY-W145636;AS-74271;CS-0226064;T1922;T73043;2,3,4,6-Tetra-O-benzyl- alpha -D-glucopyranosyl Fluoride;2-O,3-O,4-O,6-O-Tetrabenzyl-alpha-D-glucopyranosyl fluoride;(2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-fluorotetrahydro-2H-pyran;(2R,3R,4S,5R,6R)-3,4,5-TRIS(BENZYLOXY)-2-[(BENZYLOXY)METHYL]-6-FLUOROOXANE

Chemical Property of 2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl Fluoride

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 50-60 °C(lit.)
• Refractive Index: 1.6
• Boiling Point: 639.422oC at 760 mmHg
• Flash Point: >230 °F
• PSA: 46.15000
• Density: 1.206g/cm3
• LogP: 6.65380
• Storage Temp.: Refrigerator
• XLogP3: 6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 542.24685237
• Heavy Atom Count: 40
• Complexity: 669

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl Fluoride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCC2C(C(C(C(O2)F)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5
• Isomeric SMILES: C1=CC=C(C=C1)COC[C@@H]2[C@H]([C@@H]([C@H]([C@H](O2)F)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5
• Uses: 2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl Fluoride (cas# 89025-46-7) is a useful carbohydrate building block, due to its fluorine substituent, and is used for glucosylations with activated sulfonium ions, and via photocatalytic glycosylation.

Technology Process of 2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl Fluoride

There total 68 articles about 2,3,4,6-Tetra-O-benzyl-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: 99.0%

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) → 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl fluoride (78153-79-4,89025-46-7,94898-42-7,94898-43-8,101966-50-1,143615-35-4,122741-44-0)

Guidance literature:

With diethylamino-sulfur trifluoride; In tetrahydrofuran; for 0.333333h; Ambient temperature; addition at -30 deg C;

DOI:10.1016/S0040-4039(00)98451-X

Reference yield: 98.0%

phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside (38184-10-0,62774-37-2,74801-29-9,91602-61-8,116501-52-1,139974-84-8,116501-53-2) → 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl fluoride (78153-79-4,89025-46-7,94898-43-8,101966-50-1,122741-44-0,143615-35-4,94898-42-7)

Guidance literature:

With tetrafluoroboric acid; [bis(pyridine)iodine]⁺ tetrafluoroborate; In dichloromethane; at -40 ℃;

DOI:10.1021/jo7018653

Reference yield: 94.0%

(pent-4′-enyl) 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside (117841-64-2) → 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl fluoride (78153-79-4,89025-46-7,94898-43-8,101966-50-1,122741-44-0,143615-35-4,94898-42-7)

Guidance literature:

With tetrafluoroboric acid; [bis(pyridine)iodine]⁺ tetrafluoroborate; In dichloromethane; at -40 ℃; for 0.5h;

DOI:10.1021/ol070753r

upstream raw materials:

1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-mannopyranose

S-ethyl 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside

2-{[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)oxy]methyl}benzoic acid

phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside

Downstream raw materials:

methyl (2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-(1→4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

methyl 4-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)(1→4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

2,4-dimethylpentan-3-yl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

2,4-dimethylpentan-3-yl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside

Refernces

Synthesis of 1-[3,5-bis-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,4, 6-hihydroxyphenyl]ethanone : An intermediate of potential usefulness for synthesis of bis-C-glucosyl flavonoids

10.1016/S0008-6215(96)00280-7

The research aimed to synthesize 1-[3,5-bis-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,4,6-trihydroxyphenyl]ethanone, an intermediate compound that is potentially useful for the synthesis of bis-C-glucosyl flavonoids. The study focused on the bis-glycosylation of 3,5-dibenzyloxyphenol with 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl fluoride in a two-step sequence, resulting in the bis-glucosylated product, 3,5-dibenzyloxy-2,6-bis-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)phenol. The subsequent steps involved hydrogenolytic debenzylation and acetylation to yield the undeca-O-acetyl derivative, which was then subjected to Friedel-Crafts acylation with borontrifluoride-acetic acid to obtain the 4-C-acetyl target compound. The research concluded that this methodology is now available for the synthesis of bis-C-glycosyl compounds, and further syntheses of bis-C-glycosyl flavonoids are in progress.