benzyl 2,3,4-tri-O-benzyl-α-D-mannopyranuronic acid

Base Information

• Chemical Name: benzyl 2,3,4-tri-O-benzyl-α-D-mannopyranuronic acid
• CAS No.: 858352-14-4
• Molecular Formula: C₃₄H₃₄O₇
• Molecular Weight: 554.64
• Mol file: 858352-14-4.mol

Synonyms:benzyl 2,3,4-tri-O-benzyl-α-D-mannopyranuronic acid

Chemical Property of benzyl 2,3,4-tri-O-benzyl-α-D-mannopyranuronic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2,3,4-tri-O-benzyl-α-D-mannopyranuronic acid

There total 6 articles about benzyl 2,3,4-tri-O-benzyl-α-D-mannopyranuronic acid 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: 96.0%

benzyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside (57783-76-3) → benzyl 2,3,4-tri-O-benzyl-α-D-mannopyranuronic acid (858352-14-4)

Guidance literature:

With potassium dichromate; sulfuric acid; In acetone; at 55 ℃; for 2h;

DOI:10.1021/ol050774q

Reference yield:

(2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol (15548-45-5) → benzyl 2,3,4-tri-O-benzyl-α-D-mannopyranuronic acid (858352-14-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine; dmap / 7 h / 60 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C / Inert atmosphere

2.2: 12 h / 20 °C / Inert atmosphere

3.1: acetic acid; hydrogen bromide / 0.07 h / 10 - 20 °C / Inert atmosphere

4.1: potassium dichromate; sulfuric acid / acetone / 2 h / 0 - 55 °C / Inert atmosphere

With pyridine; dmap; potassium dichromate; sulfuric acid; hydrogen bromide; sodium hydride; acetic acid; In N,N-dimethyl-formamide; acetone;

DOI:10.1021/acs.jmedchem.7b00433

Reference yield:

benzyl 6-O-triphenylmethyl-α-D-mannopyranoside (77455-30-2) → benzyl 2,3,4-tri-O-benzyl-α-D-mannopyranuronic acid (858352-14-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C / Inert atmosphere

1.2: 12 h / 20 °C / Inert atmosphere

2.1: acetic acid; hydrogen bromide / 0.07 h / 10 - 20 °C / Inert atmosphere

3.1: potassium dichromate; sulfuric acid / acetone / 2 h / 0 - 55 °C / Inert atmosphere

With potassium dichromate; sulfuric acid; hydrogen bromide; sodium hydride; acetic acid; In N,N-dimethyl-formamide; acetone;

DOI:10.1021/acs.jmedchem.7b00433

upstream raw materials:

benzyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside

D-Mannose

(2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

benzyl 6-O-triphenylmethyl-α-D-mannopyranoside

Downstream raw materials:

3-O-benzyl-5-deoxy-5-C-[benzyl 2,3,4-tri-O-benzyl-7-deoxy-D-glycero-α-D-manno-heptopyranosid-7(E)-ylidene]-1,2-O-isopropylidene-α-D-xylofuranose

3-O-benzyl-5-deoxy-5-C-[benzyl 2,3,4-tri-O-benzyl-7-deoxy-α-D-manno-heptopyranosid-6-ulose-7(E)-ylidene]-1,2-O-isopropylidene-α-D-xylofuranose

dimethyl (benzyl 2,3,4-tri-O-benzyl-α-D-manno-heptopyranos-6-ulos-7-yl)phosphonate

benzyl 2,3,4-tri-O-benzyl-α-D-glycero-D-manno-heptopyranoside