pent-4-enyl 3,4-di-O-benzyl-2-O-(2-naphthylmethyl)-α-L-rhamnopyranosyl-(1→4)-2,3-di-Obenzyl-6-O-pentafluorobenzoyl-α-D-galactopyranoside

Base Information

• Chemical Name: pent-4-enyl 3,4-di-O-benzyl-2-O-(2-naphthylmethyl)-α-L-rhamnopyranosyl-(1→4)-2,3-di-Obenzyl-6-O-pentafluorobenzoyl-α-D-galactopyranoside
• CAS No.: 1428344-40-4
• Molecular Formula: C₆₃H₆₁F₅O₁₁
• Molecular Weight: 1089.16
• Mol file: 1428344-40-4.mol

Synonyms:pent-4-enyl 3,4-di-O-benzyl-2-O-(2-naphthylmethyl)-α-L-rhamnopyranosyl-(1→4)-2,3-di-Obenzyl-6-O-pentafluorobenzoyl-α-D-galactopyranoside

Chemical Property of pent-4-enyl 3,4-di-O-benzyl-2-O-(2-naphthylmethyl)-α-L-rhamnopyranosyl-(1→4)-2,3-di-Obenzyl-6-O-pentafluorobenzoyl-α-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of pent-4-enyl 3,4-di-O-benzyl-2-O-(2-naphthylmethyl)-α-L-rhamnopyranosyl-(1→4)-2,3-di-Obenzyl-6-O-pentafluorobenzoyl-α-D-galactopyranoside

There total 6 articles about pent-4-enyl 3,4-di-O-benzyl-2-O-(2-naphthylmethyl)-α-L-rhamnopyranosyl-(1→4)-2,3-di-Obenzyl-6-O-pentafluorobenzoyl-α-D-galactopyranoside 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: 78.0%

phenyl 3,4-di-O-benzyl-2-O-(2-naphthylmethyl)-1-thio-α-L-rhamnopyranoside (940006-59-7) + pent-4-enyl 2,3-di-O-benzyl-6-O-pentafluorobenzoyl-β-D-galactopyranoside (613664-71-4) → pent-4-enyl 3,4-di-O-benzyl-2-O-(2-naphthylmethyl)-α-L-rhamnopyranosyl-(1→4)-2,3-di-Obenzyl-6-O-pentafluorobenzoyl-α-D-galactopyranoside (1428344-40-4)

Guidance literature:

phenyl 3,4-di-O-benzyl-2-O-(2-naphthylmethyl)-1-thio-α-L-rhamnopyranoside; pent-4-enyl 2,3-di-O-benzyl-6-O-pentafluorobenzoyl-β-D-galactopyranoside; In toluene; for 2h;

With N-iodo-succinimide; triethylsilyl trifluoromethyl sulfonate; In diethyl ether; toluene; at -20 ℃;

DOI:10.1021/ol400430p

Reference yield:

C18H26O6S → pent-4-enyl 3,4-di-O-benzyl-2-O-(2-naphthylmethyl)-α-L-rhamnopyranosyl-(1→4)-2,3-di-Obenzyl-6-O-pentafluorobenzoyl-α-D-galactopyranoside (1428344-40-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 0 - 20 °C

2.1: trifluoroacetic acid / water; dichloromethane / 20 °C

3.1: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 0 - 20 °C

4.1: toluene / 2 h

4.2: -20 °C

With tetra-(n-butyl)ammonium iodide; sodium hydride; trifluoroacetic acid; In dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ol400430p

Reference yield:

phenyl 1-thio-α-L-rhamnopyranose (1214-98-8,105026-40-2,127061-11-4,131724-82-8) → pent-4-enyl 3,4-di-O-benzyl-2-O-(2-naphthylmethyl)-α-L-rhamnopyranosyl-(1→4)-2,3-di-Obenzyl-6-O-pentafluorobenzoyl-α-D-galactopyranoside (1428344-40-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: camphor-10-sulfonic acid / methanol / Reflux

2.1: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 0 - 20 °C

3.1: trifluoroacetic acid / water; dichloromethane / 20 °C

4.1: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 0 - 20 °C

5.1: toluene / 2 h

5.2: -20 °C

With camphor-10-sulfonic acid; tetra-(n-butyl)ammonium iodide; sodium hydride; trifluoroacetic acid; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ol400430p

upstream raw materials:

phenyl 1-thio-α-L-rhamnopyranose

C₂₃H₂₄O₄S

phenyl 3,4-di-O-benzyl-2-O-(2-naphthylmethyl)-1-thio-α-L-rhamnopyranoside

pent-4-enyl 2,3-di-O-benzyl-6-O-pentafluorobenzoyl-β-D-galactopyranoside

Downstream raw materials:

benzyl 3,4-di-O-benzyl-2-O-(2-naphthylmethyl)-α-L-rhamnopyranosyl-(1→4)-2,3-di-O-benzyl-6-O-pentafluorobenzoyl-α-D-galactopyranosyl-(1→2)-2,3-di-O-benzyl-α-L-rhamnopyranosyl-(1→4)-2,3-di-O-benzyl-6-O-pentafluorobenzoyl-α-D-galactopyranoside