diphenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside phosphate

Base Information

• Chemical Name: diphenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside phosphate
• CAS No.: 186087-99-0
• Molecular Formula: C₄₆H₄₅O₉P
• Molecular Weight: 772.832
• Mol file: 186087-99-0.mol

Synonyms:diphenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside phosphate

Chemical Property of diphenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside phosphate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diphenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside phosphate

There total 7 articles about diphenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 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: 86.0%

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) + chlorophosphoric acid diphenyl ester (2524-64-3) → diphenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside phosphate (186087-99-0)

Guidance literature:

With dmap; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1016/j.tet.2005.08.090

Reference yield:

2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside (4132-28-9,4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,78609-16-2) + chlorophosphoric acid diphenyl ester (2524-64-3) → diphenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside phosphate (186087-99-0)

Guidance literature:

With dmap; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jacs.0c04255

Reference yield:

β-D-mannopyranose pentaacetate (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5) → diphenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside phosphate (186087-99-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere

2.1: sodium methylate; methanol / 17 h / 20 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 5 h / -10 - 20 °C / Inert atmosphere

3.2: 15 h / 20 °C / Inert atmosphere

4.1: N-Bromosuccinimide; water / acetone / 4 h / 20 °C / Inert atmosphere

5.1: dmap / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

With methanol; dmap; N-Bromosuccinimide; boron trifluoride diethyl etherate; water; sodium methylate; sodium hydride; In dichloromethane; N,N-dimethyl-formamide; acetone; mineral oil;

DOI:10.1021/jacs.8b04525

upstream raw materials:

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

chlorophosphoric acid diphenyl ester

D-Mannose

β-D-mannopyranose pentaacetate

Downstream raw materials:

1-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)formic acid

1,5-anhydro-2,3,4,6-tetra-O-benzyl-α-D-manno-hexitol

6-O-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside

6-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside