dibenzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl phosphate

Base Information

• Chemical Name: dibenzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl phosphate
• CAS No.: 90357-98-5
• Molecular Formula: C₄₈H₄₉O₉P
• Molecular Weight: 800.885
• Mol file: 90357-98-5.mol

Synonyms:dibenzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl phosphate

Chemical Property of dibenzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl phosphate

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dibenzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl phosphate

There total 14 articles about dibenzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl phosphate 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: 95.0%

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate (990-91-0) + 2,3,4,6-tetra-O-benzyl-D-mannopyranose (4132-28-9,4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5) → dibenzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl phosphate (90357-98-5)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; hexane; ethylbenzene; at -78 ℃; for 3h;

DOI:10.1016/S0008-6215(97)10095-7

Reference yield: 94.0%

phosphoric acid dibenzyl ester (1623-08-1) + C47H48O7 → dibenzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl phosphate (90357-98-5)

Guidance literature:

With triphenylphosphinegold(I) triflate; In chlorobenzene; at 0 ℃; for 5h; Reagent/catalyst; Molecular sieve;

DOI:10.1021/acs.orglett.7b01158

Reference yield: 81.0%

phosphoric acid dibenzyl ester (1623-08-1) + 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetimidate (74808-09-6,90357-89-4,90358-01-3,103368-01-0,103368-04-3,103368-06-5,104048-30-8,104048-33-1,114743-70-3,132201-75-3,132748-02-8,83441-60-5) → dibenzyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl phosphate (38768-84-2,82300-58-1,90357-98-5,90358-00-2,90373-52-7) + dibenzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl phosphate (90357-98-5)

Guidance literature:

In dichloromethane; for 1h; Yields of byproduct given;

upstream raw materials:

2,3,4,6-tetra-O-benzyl-D-glucopyranose

dibenzyl phosphorofluoridate

phosphoric acid dibenzyl ester

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

Downstream raw materials:

α-D-mannopyranosyl (bis(cyclohexylammonium)phosphate)

mannose-1-phosphate

guanosine 5'-diphospho-D-mannose

3,4,6-tri-O-benzyl-D-glucal

Refernces

• 1、 Fey, Sven,Elling, Lothar,Kragl, Udo. "The cofactor Mg2+ - A key switch for effective continuous enzymatic production of GDP-mannose using recombinant GDP-mannose pyrophosphorylase". . p. 475 - 481. Retrieved 2007/10/03.
• 2、 Watanabe, Yutaka,Hyodo, Nobuyuki,Ozaki, Shoichiro. "DIBENZYL PHOSPHORFLUORIDATE, A NEW PHOSPHORYLATING AGENT". . p. 5763 - 5764. Retrieved 2007/10/02.