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

Base Information

• Chemical Name: (1R,3R,7R,8S)-9-<(benzyloxy)carbonyl>-5,5-dimethyl-2,4,6-trioxa-9-azatricyclo<6.3.0.0^3,7>undecane
• CAS No.: 98944-20-8
• Molecular Formula: C₁₇H₂₁NO₅
• Molecular Weight: 319.357

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

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

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

There total 25 articles about (1R,3R,7R,8S)-9-<(benzyloxy)carbonyl>-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,11S)-9-<(benzyloxy)carbonyl>-11-chloro-5,5-dimethyl-2,4,6-trioxa-9-azatricyclo<6.3.0.03,7>undecane (98944-19-5) → (1R,3R,7R,8S)-9-<(benzyloxy)carbonyl>-5,5-dimethyl-2,4,6-trioxa-9-azatricyclo<6.3.0.03,7>undecane (98944-20-8)

Guidance literature:

With tri-n-butyl-tin hydride; In toluene; for 24h; Heating;

DOI:10.1021/jo00225a045

Reference yield: 97.0%

N-benzyloxycarbonyl-3,6-imino-5-iodo-1,2-O-isopropylidene-3,5,6-trideoxy-α-D-glucofuranose → (1R,3R,7R,8S)-9-<(benzyloxy)carbonyl>-5,5-dimethyl-2,4,6-trioxa-9-azatricyclo<6.3.0.03,7>undecane (98944-20-8)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 3h; Heating;

DOI:10.1016/S0040-4020(01)80323-9

Reference yield: 96.0%

N-benzyloxycarbonyl-3,6-dideoxy-3,6-imino-1,2-O-isopropylidene-5-O-trifluorosulphonyl-α-D-glucofuranose (133146-04-0) → (1R,3R,7R,8S)-9-<(benzyloxy)carbonyl>-5,5-dimethyl-2,4,6-trioxa-9-azatricyclo<6.3.0.03,7>undecane (98944-20-8)

Guidance literature:

With sodium tetrahydroborate; In acetonitrile; for 72h; Ambient temperature;

DOI:10.1016/S0040-4020(01)90508-3

upstream raw materials:

N-benzyloxycarbonyl-3,6-dideoxy-3,6-imino-1,2-O-isopropylidene-5-O-trifluorosulphonyl-α-D-glucofuranose

(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

3-azido-3-deoxy-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose

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

Downstream raw materials:

(1R,3R,4R,5S)-5-<(benzyloxy)carbonyl>-3-methoxy-2-oxa-6-azabicyclo<3.3.0>octan-4-ol

(1R,3S,4R,5S)-5-<(benzyloxy)carbonyl>-3-methoxy-2-oxa-6-azabicyclo<3.3.0>octan-4-ol

(1R,3R,4R,5S)-4-(benzyloxy)-5-<(benzyloxy)carbonyl>-3-methoxy-2-oxa-6-azabicyclo<3.3.0>octane

(1R,3S,4R,5S)-4-(benzyloxy)-5-<(benzyloxy)carbonyl>-3-methoxy-2-oxa-6-azabicyclo<3.3.0>octane

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