phenyl 2-azido-4-O-benzyl-6-O-{4,6-O-benzylidene-2-deoxy-2-[(R)-3-levulinoyloxyhexadecanoylamino]-β-D-glucopyranosyl}-2-deoxy-1-thio-α-D-glucopyranoside

Base Information

• Chemical Name: phenyl 2-azido-4-O-benzyl-6-O-{4,6-O-benzylidene-2-deoxy-2-[(R)-3-levulinoyloxyhexadecanoylamino]-β-D-glucopyranosyl}-2-deoxy-1-thio-α-D-glucopyranoside
• CAS No.: 775341-77-0
• Molecular Formula: C₅₃H₇₂N₄O₁₂S
• Molecular Weight: 989.24
• Mol file: 775341-77-0.mol

Synonyms:phenyl 2-azido-4-O-benzyl-6-O-{4,6-O-benzylidene-2-deoxy-2-[(R)-3-levulinoyloxyhexadecanoylamino]-β-D-glucopyranosyl}-2-deoxy-1-thio-α-D-glucopyranoside

Chemical Property of phenyl 2-azido-4-O-benzyl-6-O-{4,6-O-benzylidene-2-deoxy-2-[(R)-3-levulinoyloxyhexadecanoylamino]-β-D-glucopyranosyl}-2-deoxy-1-thio-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2-azido-4-O-benzyl-6-O-{4,6-O-benzylidene-2-deoxy-2-[(R)-3-levulinoyloxyhexadecanoylamino]-β-D-glucopyranosyl}-2-deoxy-1-thio-α-D-glucopyranoside

There total 5 articles about phenyl 2-azido-4-O-benzyl-6-O-{4,6-O-benzylidene-2-deoxy-2-[(R)-3-levulinoyloxyhexadecanoylamino]-β-D-glucopyranosyl}-2-deoxy-1-thio-α-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: 92.0%

(R)-3-levulinoyloxyhexadecanoic acid (775341-76-9) + phenyl 6-O-(2-amino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-2-azido-4-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside (548486-23-3) → phenyl 2-azido-4-O-benzyl-6-O-{4,6-O-benzylidene-2-deoxy-2-[(R)-3-levulinoyloxyhexadecanoylamino]-β-D-glucopyranosyl}-2-deoxy-1-thio-α-D-glucopyranoside (775341-77-0)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/ol048746f

Reference yield:

(R)-3-(levulinoyloxy)hexadecanoic acid 2-(4-bromophenyl)-2-oxoethyl ester (775341-89-4) → phenyl 2-azido-4-O-benzyl-6-O-{4,6-O-benzylidene-2-deoxy-2-[(R)-3-levulinoyloxyhexadecanoylamino]-β-D-glucopyranosyl}-2-deoxy-1-thio-α-D-glucopyranoside (775341-77-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / zinc / acetic acid / 2 h / 60 °C

2: 92 percent / dicyclohexylcarbodiimide / CH₂Cl₂ / 16 h / 20 °C

With dicyclohexyl-carbodiimide; zinc; In dichloromethane; acetic acid;

DOI:10.1021/ol048746f

Reference yield:

levulinic acid (123-76-2) → phenyl 2-azido-4-O-benzyl-6-O-{4,6-O-benzylidene-2-deoxy-2-[(R)-3-levulinoyloxyhexadecanoylamino]-β-D-glucopyranosyl}-2-deoxy-1-thio-α-D-glucopyranoside (775341-77-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / DCC; DMAP / CH₂Cl₂ / 3 h

2: 98 percent / zinc / acetic acid / 2 h / 60 °C

3: 92 percent / dicyclohexylcarbodiimide / CH₂Cl₂ / 16 h / 20 °C

With dmap; dicyclohexyl-carbodiimide; zinc; In dichloromethane; acetic acid;

DOI:10.1021/ol048746f

upstream raw materials:

(R)-3-levulinoyloxyhexadecanoic acid

phenyl 6-O-(2-amino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-2-azido-4-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

(R)-3-(levulinoyloxy)hexadecanoic acid 2-(4-bromophenyl)-2-oxoethyl ester

levulinic acid

Downstream raw materials:

4-oxo-pentanoic acid 1-({6-[3-benzyloxy-5-(3-benzyloxy-hexadecanoylamino)-4-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethoxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ylcarbamoyl}-methyl)-tetradecyl ester

phenyl 2-amino-4-O-benzyl-6-O-{4,6-O-benzylidene-2-deoxy-2-[(R)-3-levulinoyloxyhexadecanoylamino]-β-D-glucopyranosyl}-2-deoxy-1-thio-α-D-glucopyranoside