3-[(benzyloxycarbonyl)amino]-3-deoxy-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose

Base Information

• Chemical Name: 3-[(benzyloxycarbonyl)amino]-3-deoxy-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose
• CAS No.: 1414607-58-1
• Molecular Formula: C₁₉H₂₇NO₁₁S₂
• Molecular Weight: 509.555
• Mol file: 1414607-58-1.mol

Synonyms:3-[(benzyloxycarbonyl)amino]-3-deoxy-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose

Chemical Property of 3-[(benzyloxycarbonyl)amino]-3-deoxy-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[(benzyloxycarbonyl)amino]-3-deoxy-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose

There total 1 articles about 3-[(benzyloxycarbonyl)amino]-3-deoxy-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose 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: 95.0%

methanesulfonyl chloride (124-63-0) + [(3aR,5S,6S,6aR)-5-((R)-1,2-Dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-carbamic acid benzyl ester (37073-89-5) → 3-[(benzyloxycarbonyl)amino]-3-deoxy-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose (1414607-58-1)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 3.16667h; Inert atmosphere;

DOI:10.1055/s-0032-1316612

Reference yield: 90.0%

3-[(benzyloxycarbonyl)amino]-3-deoxy-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose (1414607-58-1) → (1S,3R,7R,8S,11R)-9-<(benzyloxy)carbonyl>-11-<(methylsulfonyl)oxy>-5,5-dimethyl-2,4,6-trioxa-9-azatricyclo<6.3.0.03,7>undecane (84730-22-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1055/s-0032-1316612

Reference yield:

3-[(benzyloxycarbonyl)amino]-3-deoxy-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose (1414607-58-1) → C14H16N4O5 (1414607-46-7)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere

2: sodium azide / N,N-dimethyl-formamide / 24 h / 90 °C / Inert atmosphere

3: water; trifluoroacetic acid / 3.25 h / 0 - 25 °C

With sodium azide; water; sodium hydride; trifluoroacetic acid; In N,N-dimethyl-formamide;

DOI:10.1055/s-0032-1316612

upstream raw materials:

methanesulfonyl chloride

[(3aR,5S,6S,6aR)-5-((R)-1,2-Dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-carbamic acid benzyl ester

Downstream raw materials:

(1S,3R,7R,8S,11R)-9-<(benzyloxy)carbonyl>-11-<(methylsulfonyl)oxy>-5,5-dimethyl-2,4,6-trioxa-9-azatricyclo<6.3.0.0^3,7>undecane

benzyl (3aR,4aS,5S,7aS,7bR)-5-azido-2,2-dimethylhexahydro-7H-[1,3]dioxolo[4,5]furo[3,2-b]pyrrole-7-carboxylate

C₁₄H₁₆N₄O₅

C₁₃H₁₄N₄O₄