(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

Base Information

• Chemical Name: (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
• CAS No.: 84730-22-3
• Molecular Formula: C₁₈H₂₃NO₈S
• Molecular Weight: 413.449

Synonyms:(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

Chemical Property of (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

Chemical Property:

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• Pictogram(s):  
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Technology Process of (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

There total 7 articles about (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 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: 100.0%

(1S,3R,7R,8S,11R)-11-<(methylsulfonyl)oxy>-5,5-dimethyl-2,4,6-trioxa-9-azatricyclo<6.3.0.03,7>undecane (98944-18-4) + 2-benzyloxycarbonylsulfanyl-4,6-dimethyl-pyrimidine (42116-21-2) → (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 triethylamine; In methanol; for 2h; Ambient temperature;

DOI:10.1021/jo00225a045

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: 90.0%

methanesulfonyl chloride (124-63-0) + 3,6-<(benzyloxycarbonyl)imino>-3,6-dideoxy-1,2-O-isopropylidene-α-D-glucofuranose (84730-21-2,84730-24-5,105879-02-5) → 3,6-(benzyloxycarbonyl)imino-3,6-dideoxy-1,2-O-isopropylidene-5-O-(methylsulfonyl)-α-D-glucofuranose (84730-22-3)

Guidance literature:

In pyridine; Ambient temperature;

DOI:10.1016/0008-6215(83)88284-6

upstream raw materials:

methanesulfonyl chloride

3,6-<(benzyloxycarbonyl)imino>-3,6-dideoxy-1,2-O-isopropylidene-α-D-glucofuranose

3-azido-3-deoxy-1,2:5,6-di-(O-isopropylidene)-α-D-glucofuranose

benzyl chloroformate

Downstream raw materials:

5-O-benzoyl-3,6-(benzyloxycarbonyl)imino-3,6-dideoxy-1,2-O-isopropylidene-β-L-idofuranose

(1S,3R,7R,8S,11S)-9-<(benzyloxy)carbonyl>-11-chloro-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

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