methyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-β-D-mannopyranoside

Base Information

• Chemical Name: methyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-β-D-mannopyranoside
• CAS No.: 855306-46-6
• Molecular Formula: C₁₇H₂₀O₆
• Molecular Weight: 320.342
• Mol file: 855306-46-6.mol

Synonyms:methyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-β-D-mannopyranoside

Chemical Property of methyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-β-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-β-D-mannopyranoside

There total 5 articles about methyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-β-D-mannopyranoside 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%

methyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-p-methoxybenzyl-β-D-mannopyranoside (855306-45-5) → methyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-β-D-mannopyranoside (855306-46-6)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃; for 3h;

DOI:10.1021/ol050680g DOI:10.1021/jo0526789

Reference yield: 89.0%

methyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl)-2-O-(prop-2-ynyl)-β-D-mannopyranoside (951025-08-4) → methyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-β-D-mannopyranoside (855306-46-6)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/jo071009n

Reference yield:

phenyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl)-2-O-(prop-2-ynyl)-1-thio-α-D-mannopyranoside (951025-07-3) → methyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-β-D-mannopyranoside (855306-46-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: BSP; TTBP; Tf₂O / CH₂Cl₂ / 0.5 h / -60 °C

1.2: 85 percent / CH₂Cl₂ / 2 h / -60 °C

2.1: 89 percent / DDQ / CH₂Cl₂ / 3 h / 20 °C

With trifluoromethylsulfonic anhydride; sulfobromophthalein sodium; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane;

DOI:10.1021/jo071009n

upstream raw materials:

methyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-p-methoxybenzyl-β-D-mannopyranoside

methyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl)-2-O-(prop-2-ynyl)-β-D-mannopyranoside

phenyl 4,6-O-benzylidene-3-O-(2-methylnaphthyl)-1-thio-α-D-mannopyranoside

phenyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl)-2-O-(prop-2-ynyl)-1-thio-α-D-mannopyranoside

Downstream raw materials:

methyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(2-naphthylmethyl)-β-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-2-O-(prop-2-ynyl)-β-D-mannopyranosyl-(1->3)-4,6-benzylidene-2-O-(prop-2-ynyl)-β-D-mannopyranoside

methyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-2-O-(prop-2-ynyl)-β-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-2-O-(prop-2-ynyl)-β-D-mannopyranoside