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

Base Information

• Chemical Name: 2,3,4,6-Tetra-O-benzyl-D-glucopyranosyl Fluoride
• CAS No.: 122741-44-0
• Molecular Formula: C₃₄H₃₅FO₅
• Molecular Weight: 542.647
• DSSTox Substance ID: DTXSID40449454
• Nikkaji Number: J967.157I
• Mol file: 122741-44-0.mol

Synonyms:122741-44-0;2,3,4,6-Tetra-O-benzyl-D-glucopyranosyl Fluoride;D-Glucopyranosyl fluoride, 2,3,4,6-tetrakis-O-(phenylmethyl)-;(3R,4S,5R,6R)-2-fluoro-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane;SCHEMBL2124872;DTXSID40449454;QNXIKNZDQVSBCO-BKJHVTENSA-N;AKOS037646847;HY-W145533;AS-71162;CS-0214498;T1971;E78804;A891021;2-O,3-O,4-O,6-O-Tetrabenzyl-D-glucopyranosyl fluoride;2,3,4,6-tetra-O-benzyl-alpha/beta-D-glucopyranosyl fluoride;(2R,3R,4S,5R)-3,4,5-TRIS(BENZYLOXY)-2-[(BENZYLOXY)METHYL]-6-FLUOROOXANE

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

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 50-60 °C(lit.)
• Refractive Index: 28 ° (C=1, CHCl3)
• Boiling Point: 639.422°C at 760 mmHg
• Flash Point: 351.978°C
• 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-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(O2)F)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5
• Uses: (3R,4S,5R,6R)-2-fluoro-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane is a useful carbohydrate building block, used in the synthetic preparation of pharmacologically active compounds such as mangiferin, homomangiferin, and neomangiferin.

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

There total 48 articles about 2,3,4,6-Tetra-O-benzyl-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-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-α-D-glucopyranoside

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

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

Refernces

• 1、 Bannykh, Anton,Khomutnyk, Yaroslav,Kim, Sungjin,Nagorny, Pavel. "Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride". supporting information. p. 190 - 194. Retrieved 2021/01/13.
• 2、 Wei, Xiong,Liang, Danlin,Wang, Qing,Meng, Xiangbao,Li, Zhongjun. "Total synthesis of mangiferin, homomangiferin, and neomangiferin". . p. 8821 - 8831. Retrieved 2016/10/03.