[(1R,2R,3S,4R,5R,6S)-3-(Benzyloxycarbonyl-methyl-amino)-2,4,6-trihydroxy-5-((3aR,4S,6R,7aR)-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-cyclohexyl]-methyl-carbamic acid benzyl ester

Base Information

Chemical Name:[(1R,2R,3S,4R,5R,6S)-3-(Benzyloxycarbonyl-methyl-amino)-2,4,6-trihydroxy-5-((3aR,4S,6R,7aR)-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-cyclohexyl]-methyl-carbamic acid benzyl ester
CAS No.:96680-97-6
Molecular Formula:C₃₃H₄₄N₂O₁₁
Molecular Weight:644.719
Hs Code.:

[(1R,2R,3S,4R,5R,6S)-3-(Benzyloxycarbonyl-methyl-amino)-2,4,6-trihydroxy-5-((3aR,4S,6R,7aR)-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-cyclohexyl]-methyl-carbamic acid benzyl ester

Synonyms:[(1R,2R,3S,4R,5R,6S)-3-(Benzyloxycarbonyl-methyl-amino)-2,4,6-trihydroxy-5-((3aR,4S,6R,7aR)-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-cyclohexyl]-methyl-carbamic acid benzyl ester

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Chemical Property of [(1R,2R,3S,4R,5R,6S)-3-(Benzyloxycarbonyl-methyl-amino)-2,4,6-trihydroxy-5-((3aR,4S,6R,7aR)-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-cyclohexyl]-methyl-carbamic acid benzyl ester

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Technology Process of [(1R,2R,3S,4R,5R,6S)-3-(Benzyloxycarbonyl-methyl-amino)-2,4,6-trihydroxy-5-((3aR,4S,6R,7aR)-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-cyclohexyl]-methyl-carbamic acid benzyl ester

There total 13 articles about [(1R,2R,3S,4R,5R,6S)-3-(Benzyloxycarbonyl-methyl-amino)-2,4,6-trihydroxy-5-((3aR,4S,6R,7aR)-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-cyclohexyl]-methyl-carbamic acid benzyl ester 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: 78.0%

: 64979-14-2,72244-45-2
N,N'-<(benzyloxy)carbonyl>-4(R),4a(R)-tetrahydrospectinomycin

: 77-76-9
2,2-dimethoxy-propane

: 96680-97-6
[(1R,2R,3S,4R,5R,6S)-3-(Benzyloxycarbonyl-methyl-amino)-2,4,6-trihydroxy-5-((3aR,4S,6R,7aR)-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-cyclohexyl]-methyl-carbamic acid benzyl ester

Guidance literature:: With toluene-4-sulfonic acid; In benzene; at 25 ℃; for 1h;
DOI:10.1139/v85-026

Reference yield:

: 64979-02-8
N,N'-<(benzyloxy)carbonyl>actinamine

: 96680-97-6
[(1R,2R,3S,4R,5R,6S)-3-(Benzyloxycarbonyl-methyl-amino)-2,4,6-trihydroxy-5-((3aR,4S,6R,7aR)-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-cyclohexyl]-methyl-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 62 percent / silver trifluoromethanesulfonate / tetrahydrofuran / 3 h / -40 °C

2: 1.) sodium metal, 2.) Dowex-50 (H+) / methanol / 1.) 0 deg C, 15 min, 2.) 25 deg C

3: 78 percent / p-TsOH / benzene / 1 h / 25 °C

With Dowex-50 (H+); sodium; toluene-4-sulfonic acid; silver trifluoromethanesulfonate; In tetrahydrofuran; methanol; benzene;
DOI:10.1139/v85-026

Reference yield:

: 21736-83-4
(+)-spectinomycin dihydrochloride

: 96680-97-6
[(1R,2R,3S,4R,5R,6S)-3-(Benzyloxycarbonyl-methyl-amino)-2,4,6-trihydroxy-5-((3aR,4S,6R,7aR)-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-cyclohexyl]-methyl-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: Dowex-1 (OH-)

2: H₂ / catalytic hydrogenation

3: 97 percent / pyridine / 18 h / 0 °C

4: 9 percent / silver carbonate / acetone; H₂O

5: 62 percent / silver trifluoromethanesulfonate / tetrahydrofuran / 3 h / -40 °C

6: 1.) sodium metal, 2.) Dowex-50 (H+) / methanol / 1.) 0 deg C, 15 min, 2.) 25 deg C

7: 78 percent / p-TsOH / benzene / 1 h / 25 °C

With Dowex-1 (OH-); Dowex-50 (H+); hydrogen; sodium; toluene-4-sulfonic acid; silver carbonate; silver trifluoromethanesulfonate; In tetrahydrofuran; pyridine; methanol; water; acetone; benzene;
DOI:10.1139/v85-026