4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphth-ylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-6-O-levulinyl-L-idopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphth-ylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-6-O-levulinyl-L-idopyranosyl trichloroacetimidate
• CAS No.: 657395-07-8
• Molecular Formula: C₅₈H₅₅Cl₃N₄O₁₄
• Molecular Weight: 1138.45
• Mol file: 657395-07-8.mol

Synonyms:4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphth-ylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-6-O-levulinyl-L-idopyranosyl trichloroacetimidate

Chemical Property of 4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphth-ylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-6-O-levulinyl-L-idopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphth-ylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-6-O-levulinyl-L-idopyranosyl trichloroacetimidate

There total 24 articles about 4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphth-ylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-6-O-levulinyl-L-idopyranosyl 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: 89.0%

trichloroacetonitrile (545-06-2) + 4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-6-O-levulinyl-L-idopyranose → 4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphth-ylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-6-O-levulinyl-L-idopyranosyl trichloroacetimidate (657395-07-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 3h; Inert atmosphere; Cooling with ice;

DOI:10.1039/c1ob06415k

Reference yield:

1,6-anhydro-2-O-benzoyl-3-O-benzyl-β-L-idopyranoside (334834-19-4) → 4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphth-ylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-6-O-levulinyl-L-idopyranosyl trichloroacetimidate (657395-07-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 61 percent / TMSOTf

2: 88 percent / Cu(OTf)2

3: 81 percent / PTSA

4: 97 percent / pyridine

5: NH₃(g)

6: DBU

With pyridine; trimethylsilyl trifluoromethanesulfonate; ammonia; copper(II) bis(trifluoromethanesulfonate); toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene;

DOI:10.1002/jccs.200400175

Reference yield:

3-O-benzyl-1,6-anhydro-β-L-idopyranose (42926-91-0) → 4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphth-ylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-6-O-levulinyl-L-idopyranosyl trichloroacetimidate (657395-07-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / pyridine

2: 61 percent / TMSOTf

3: 88 percent / Cu(OTf)2

4: 81 percent / PTSA

5: 97 percent / pyridine

6: NH₃(g)

7: DBU

With pyridine; trimethylsilyl trifluoromethanesulfonate; ammonia; copper(II) bis(trifluoromethanesulfonate); toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene;

DOI:10.1002/jccs.200400175

upstream raw materials:

trichloroacetonitrile

6-hydroxy-1,2:3,5-di-O-isopropylidene-α-D-glucofuranoside

6-deoxy-1,2:3,5-di-O-isopropylidene-α-D-xylo-hex-5-enofuranose

levulinic anhydride

Downstream raw materials:

C₁₂₂H₁₂₁N₉O₃₂

methyl [2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-(1->4)-(2-O-benzoyl-3-O-benzyl-6-O-levulinyl-α-L-idopyranosyl)-(1->4)-2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-α-D-glucopyranoside