(1R,2R,6R,8R,12S,14S)-12-benzyloxycarbonylmethyl-10,13-diaza-4,4-dimethyl-16,16-dioxide-11-oxo-3,5,7,17-tetraoxa-16-thio-pentacyclo[9.6.0.0^2,6.0^1,14.0^10,14]heptadecane

Base Information

• Chemical Name: (1R,2R,6R,8R,12S,14S)-12-benzyloxycarbonylmethyl-10,13-diaza-4,4-dimethyl-16,16-dioxide-11-oxo-3,5,7,17-tetraoxa-16-thio-pentacyclo[9.6.0.0^2,6.0^1,14.0^10,14]heptadecane
• CAS No.: 911429-70-4
• Molecular Formula: C₂₁H₂₄N₂O₉S
• Molecular Weight: 480.496

Synonyms:(1R,2R,6R,8R,12S,14S)-12-benzyloxycarbonylmethyl-10,13-diaza-4,4-dimethyl-16,16-dioxide-11-oxo-3,5,7,17-tetraoxa-16-thio-pentacyclo[9.6.0.0^2,6.0^1,14.0^10,14]heptadecane

Chemical Property of (1R,2R,6R,8R,12S,14S)-12-benzyloxycarbonylmethyl-10,13-diaza-4,4-dimethyl-16,16-dioxide-11-oxo-3,5,7,17-tetraoxa-16-thio-pentacyclo[9.6.0.0^2,6.0^1,14.0^10,14]heptadecane

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Technology Process of (1R,2R,6R,8R,12S,14S)-12-benzyloxycarbonylmethyl-10,13-diaza-4,4-dimethyl-16,16-dioxide-11-oxo-3,5,7,17-tetraoxa-16-thio-pentacyclo[9.6.0.0^2,6.0^1,14.0^10,14]heptadecane

There total 7 articles about (1R,2R,6R,8R,12S,14S)-12-benzyloxycarbonylmethyl-10,13-diaza-4,4-dimethyl-16,16-dioxide-11-oxo-3,5,7,17-tetraoxa-16-thio-pentacyclo[9.6.0.0^2,6.0^1,14.0^10,14]heptadecane 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: 63.0%

5,N4cyclo-3-spiro-5'-(4'-amino-1',2'-oxathiole-2',2'-dioxide)-1,2-O-isopropilidene-α-D-ribofuranose (911429-56-6) + L-aspartic acid dibenzyl ester hydrochloride (6327-59-9,174457-99-9) → (1R,2R,6R,8R,12S,14S)-12-benzyloxycarbonylmethyl-10,13-diaza-4,4-dimethyl-16,16-dioxide-11-oxo-3,5,7,17-tetraoxa-16-thio-pentacyclo[9.6.0.02,6.01,14.010,14]heptadecane (911429-70-4)

Guidance literature:

With triethylamine; In acetonitrile; for 4h; Heating;

DOI:10.1021/jo0609531

Reference yield:

Toluene-4-sulfonic acid (3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester (1054652-94-6) → (1R,2R,6R,8R,12S,14S)-12-benzyloxycarbonylmethyl-10,13-diaza-4,4-dimethyl-16,16-dioxide-11-oxo-3,5,7,17-tetraoxa-16-thio-pentacyclo[9.6.0.02,6.01,14.010,14]heptadecane (911429-70-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 67 percent / pyridine / 5 °C

2: 60 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0.33 h / 0 °C

3: 90 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0.17 h / 80 °C

4: 63 percent / triethylamine / acetonitrile / 4 h / Heating

With pyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In acetonitrile;

DOI:10.1021/jo0609531

Reference yield:

3-C-cyano-1,2-O-isopropylidene-3-O-mesyl-5-O-tosyl-α-D-ribofuranose (911429-57-7) → (1R,2R,6R,8R,12S,14S)-12-benzyloxycarbonylmethyl-10,13-diaza-4,4-dimethyl-16,16-dioxide-11-oxo-3,5,7,17-tetraoxa-16-thio-pentacyclo[9.6.0.02,6.01,14.010,14]heptadecane (911429-70-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0.33 h / 0 °C

2: 90 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0.17 h / 80 °C

3: 63 percent / triethylamine / acetonitrile / 4 h / Heating

With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In acetonitrile;

DOI:10.1021/jo0609531

upstream raw materials:

5,N⁴cyclo-3-spiro-5'-(4'-amino-1',2'-oxathiole-2',2'-dioxide)-1,2-O-isopropilidene-α-D-ribofuranose

L-aspartic acid dibenzyl ester hydrochloride

Toluene-4-sulfonic acid (3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester

3-C-cyano-1,2-O-isopropylidene-3-O-mesyl-5-O-tosyl-α-D-ribofuranose

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