2-azidoethyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->2)-3,4-O-isopropylidene-α-D-fucopyranoside

Base Information

• Chemical Name: 2-azidoethyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->2)-3,4-O-isopropylidene-α-D-fucopyranoside
• CAS No.: 1220051-61-5
• Molecular Formula: C₄₅H₅₃N₃O₁₀
• Molecular Weight: 795.93
• Mol file: 1220051-61-5.mol

Synonyms:2-azidoethyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->2)-3,4-O-isopropylidene-α-D-fucopyranoside

Chemical Property of 2-azidoethyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->2)-3,4-O-isopropylidene-α-D-fucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-azidoethyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->2)-3,4-O-isopropylidene-α-D-fucopyranoside

There total 4 articles about 2-azidoethyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->2)-3,4-O-isopropylidene-α-D-fucopyranoside 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: 76.0%

2-azidoethyl 3,4-O-isopropylidene-α-D-fucopyranoside (1220051-58-0) + ethyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside (125411-99-6) → 2-azidoethyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->2)-3,4-O-isopropylidene-α-D-fucopyranoside (1220051-61-5)

Guidance literature:

With tetrabutylammomium bromide; copper(ll) bromide; In 1,2-dichloro-ethane; N,N-dimethyl-formamide; at 20 ℃; for 48h; stereoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1080/07328300903428989

Reference yield:

C8H15N3O5 → 2-azidoethyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->2)-3,4-O-isopropylidene-α-D-fucopyranoside (1220051-61-5)

Guidance literature:

Multi-step reaction with 2 steps

1: acetone / 2 h / 20 °C

2: tetrabutylammomium bromide; copper(ll) bromide / 1,2-dichloro-ethane; N,N-dimethyl-formamide / 48 h / 20 °C / Molecular sieve; Inert atmosphere

With tetrabutylammomium bromide; copper(ll) bromide; In 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone;

DOI:10.1080/07328300903428989

Reference yield:

1,2:3,4-di-O-isopropylidene-α-D-fucopyranose (4026-27-1) → 2-azidoethyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->2)-3,4-O-isopropylidene-α-D-fucopyranoside (1220051-61-5)

Guidance literature:

Multi-step reaction with 4 steps

1: acetic acid / water / 6 h / 80 °C

2: silica-supported perchloric acid / 50 h / 80 °C

3: acetone / 2 h / 20 °C

4: tetrabutylammomium bromide; copper(ll) bromide / 1,2-dichloro-ethane; N,N-dimethyl-formamide / 48 h / 20 °C / Molecular sieve; Inert atmosphere

With tetrabutylammomium bromide; acetic acid; copper(ll) bromide; In water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; 2: Fischer glycosylation;

DOI:10.1080/07328300903428989

upstream raw materials:

2-azidoethyl 3,4-O-isopropylidene-α-D-fucopyranoside

ethyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside

D-Fucose

1,2:3,4-di-O-isopropylidene-α-D-fucopyranose

Downstream raw materials:

2-azidoethyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->2)-4-O-acetyl-α-D-fucopyranoside

2-azidoethyl (2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl)-(1->3)-[(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->2)]-4-O-acetyl-α-D-fucopyranoside