tert-butyldimethylsilyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: tert-butyldimethylsilyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 153094-02-1
• Molecular Formula: C₃₃H₄₉N₃O₁₄Si
• Molecular Weight: 739.849
• Mol file: 153094-02-1.mol

Synonyms:

Chemical Property of tert-butyldimethylsilyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyldimethylsilyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside

There total 6 articles about tert-butyldimethylsilyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside 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:

2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate (86520-63-0) + tert-Butyldimethylsilyl 2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside (153094-00-9) → tert-butyldimethylsilyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside (136505-41-4) + tert-butyldimethylsilyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside (153094-02-1)

Guidance literature:

With boron trifluoride diethyl etherate; In hexane; dichloromethane; at -25 ℃; for 1h; Yield given. Yields of byproduct given;

Reference yield:

tert-Butyldimethylsilyl 2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside (153094-00-9) + Trichloro-acetic acid (2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl ester → tert-butyldimethylsilyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside (136505-41-4) + tert-butyldimethylsilyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside (153094-02-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃;

DOI:10.1016/S0957-4166(00)00342-6

Reference yield:

tert-Butyldimethylsilyl-2-azido-2-desoxy-β-D-glucopyranosid (99049-67-9) → tert-butyldimethylsilyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside (153094-02-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) bis(tributyltin) oxide, 2.) tetrabutylammonium iodide / 1.) toluene, reflux, 2.5 h, 2.) 8 h, 95 deg C

2: 0.05M methyl trifluoromethanesulfonate / diethyl ether / Ambient temperature

With tetra-(n-butyl)ammonium iodide; bis(tri-n-butyltin)oxide; methyl trifluoromethanesulfonate; In diethyl ether;

upstream raw materials:

2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate

tert-Butyldimethylsilyl 2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside

tert-Butyldimethylsilyl-2-azido-2-desoxy-β-D-glucopyranosid

benzyl bromide

Downstream raw materials:

tert-butyldimethylsilyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)>-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside