2,3,4,6-Tetra-O-benzyl-D-mannopyranosylfluoride

Base Information

• Chemical Name: 2,3,4,6-Tetra-O-benzyl-D-mannopyranosylfluoride
• CAS No.: 94898-42-7
• Molecular Formula: C₃₄H₃₅FO₅
• Molecular Weight: 542.647
• Hs Code.: 2938909090
• Mol file: 94898-42-7.mol

Synonyms:2,3,4,6-Tetrakis-O-(phenylMethyl)-α-D-Mannopyranosyl Fluoride

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

Chemical Property:

• PSA: 46.15000
• LogP: 6.65380

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2,3,4,6-Tetra-O-benzyl-D-mannopyranosyl Fluoride (cas# 94898-42-7) is a compound useful in organic synthesis.

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

There total 48 articles about 2,3,4,6-Tetra-O-benzyl-D-mannopyranosylfluoride 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.