O-(2-deoxy-2-azido-3,4,6-tri-O-benzyl-α-D-galactopyranosyl) trichloroacetimidate

Base Information

• Chemical Name: O-(2-deoxy-2-azido-3,4,6-tri-O-benzyl-α-D-galactopyranosyl) trichloroacetimidate
• CAS No.: 94715-55-6
• Molecular Formula: C₂₉H₂₉Cl₃N₄O₅
• Molecular Weight: 619.932
• Mol file: 94715-55-6.mol

Synonyms:O-(2-deoxy-2-azido-3,4,6-tri-O-benzyl-α-D-galactopyranosyl) trichloroacetimidate

Chemical Property of O-(2-deoxy-2-azido-3,4,6-tri-O-benzyl-α-D-galactopyranosyl) trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(2-deoxy-2-azido-3,4,6-tri-O-benzyl-α-D-galactopyranosyl) trichloroacetimidate

There total 8 articles about O-(2-deoxy-2-azido-3,4,6-tri-O-benzyl-α-D-galactopyranosyl) trichloroacetimidate 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: 75.0%

2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-galactopyranose (79781-69-4) + trichloroacetonitrile (545-06-2) → O-(2-deoxy-2-azido-3,4,6-tri-O-benzyl-α-D-galactopyranosyl) trichloroacetimidate (94715-55-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 30 ℃; for 1h;

DOI:10.1021/jo971727h

Reference yield:

2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-galactopyranose (79781-69-4) + trichloroacetonitrile (545-06-2) → O-(2-deoxy-2-azido-3,4,6-tri-O-benzyl-α-D-galactopyranosyl) trichloroacetimidate (94715-55-6) + 3,4,6-tri-O-benzyl-2-deoxy-2-azido-β-D-galactopyranosyl 2,2,2-trichloroacetimidate (205593-86-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 1h; Overall yield = 83 %; Overall yield = 1.24 g;

DOI:10.3762/bjoc.14.258

Reference yield:

3,4,6-tri-O-benzyl-2-deoxy-2-azido-α/β-D-galactopyranosyl nitrate → O-(2-deoxy-2-azido-3,4,6-tri-O-benzyl-α-D-galactopyranosyl) trichloroacetimidate (94715-55-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / NaNO₂, H₂O / dioxane / 80 °C

2: NaH / CH₂Cl₂ / 4 h / Ambient temperature

With water; sodium hydride; sodium nitrite; In 1,4-dioxane; dichloromethane;

DOI:10.1002/hlca.19870700516

upstream raw materials:

2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-galactopyranose

trichloroacetonitrile

C₃₄H₃₅N₃O₄S

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose

Downstream raw materials:

dimethyl (2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl) phosphonate

dimethyl (2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl) phosphonate

2-((2S,3R,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylsulfanyl)-pyridine

2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-galactopyranosyl-α(1->6)-4,5-O-(1',2'-dimethoxycyclohexane-1',2'-diyl)-1,2-O-isopropylidene-3-O-methyl-D-chiro-inositol