(2S,3R,4E) 2-azido-3-(benzoyloxy)-1-O-<(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyloxy>-4-octadecene

Base Information

• Chemical Name: (2S,3R,4E) 2-azido-3-(benzoyloxy)-1-O-<(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyloxy>-4-octadecene
• CAS No.: 137915-45-8
• Molecular Formula: C₆₃H₈₉N₃O₂₈
• Molecular Weight: 1336.4
• Mol file: 137915-45-8.mol

Synonyms:(2S,3R,4E) 2-azido-3-(benzoyloxy)-1-O-<(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyloxy>-4-octadecene

Chemical Property of (2S,3R,4E) 2-azido-3-(benzoyloxy)-1-O-<(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyloxy>-4-octadecene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4E) 2-azido-3-(benzoyloxy)-1-O-<(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyloxy>-4-octadecene

There total 3 articles about (2S,3R,4E) 2-azido-3-(benzoyloxy)-1-O-<(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyloxy>-4-octadecene 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: 66.0%

(2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol (103348-50-1) + O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1→4)-O-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl trichloroacetimidate (113421-48-0) → (2S,3R,4E) 2-azido-3-(benzoyloxy)-1-O-<(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyloxy>-4-octadecene (137915-45-8)

Guidance literature:

With 3 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at 25 ℃; for 2h;

DOI:10.1016/S0008-6215(99)00230-X

Reference yield:

O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1→4)-O-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-acetyl-D-glucopyranose (137896-81-2,137896-82-3,150965-56-3,150965-60-9) → (2S,3R,4E) 2-azido-3-(benzoyloxy)-1-O-<(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyloxy>-4-octadecene (137915-45-8)

Guidance literature:

Multi-step reaction with 2 steps

1: DBU

2: 60 percent / BF₃*Et₂O, molecular sieves / CH₂Cl₂; hexane / 2 h / Ambient temperature

With molecular sieve; boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In hexane; dichloromethane;

Reference yield:

O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1-4)-O-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-acetyl-α-and-β-D-glucopyranosyl acetate (116182-08-2) → (2S,3R,4E) 2-azido-3-(benzoyloxy)-1-O-<(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyloxy>-4-octadecene (137915-45-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / hydrazinium acetate / dimethylformamide / 3 h / 50 °C

2: DBU

3: 60 percent / BF₃*Et₂O, molecular sieves / CH₂Cl₂; hexane / 2 h / Ambient temperature

With molecular sieve; boron trifluoride diethyl etherate; hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In hexane; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

(2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol

O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1→4)-O-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl trichloroacetimidate

O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1→4)-O-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-acetyl-D-glucopyranose

O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1-4)-O-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-acetyl-α-and-β-D-glucopyranosyl acetate

Downstream raw materials:

(2S,3R,4E) 2-azido-3-(benzoyloxy)-2-(hexadecanoylamino)-1-O-<(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyloxy>-4-octadecene

Refernces

• 1、 Qiu, Dongxu,Schmidt, Richard R.. "Synthesis of Globotriaosylceramide (Gb3) and Isoglobotriaosylceramide (isoGb3)". . p. 217 - 224. Retrieved 2007/10/02.