(2R,3R,5S,8R,10S)-2-[(1R,3S)-7-((2S,3S,5R,6S)-3,5-Dimethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl)-3-methyl-5-oxo-1-triethylsilanyloxy-oct-7-enyl]-8,10-dimethyl-3-triethylsilanyloxy-1-oxa-6-aza-spiro[4.5]decane-6-carboxylic acid propyl ester

Base Information

Chemical Name:(2R,3R,5S,8R,10S)-2-[(1R,3S)-7-((2S,3S,5R,6S)-3,5-Dimethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl)-3-methyl-5-oxo-1-triethylsilanyloxy-oct-7-enyl]-8,10-dimethyl-3-triethylsilanyloxy-1-oxa-6-aza-spiro[4.5]decane-6-carboxylic acid propyl ester
CAS No.:910789-69-4
Molecular Formula:C₄₈H₈₃NO₇SSi₂
Molecular Weight:874.427
Hs Code.:

(2R,3R,5S,8R,10S)-2-[(1R,3S)-7-((2S,3S,5R,6S)-3,5-Dimethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl)-3-methyl-5-oxo-1-triethylsilanyloxy-oct-7-enyl]-8,10-dimethyl-3-triethylsilanyloxy-1-oxa-6-aza-spiro[4.5]decane-6-carboxylic acid propyl ester

Synonyms:(2R,3R,5S,8R,10S)-2-[(1R,3S)-7-((2S,3S,5R,6S)-3,5-Dimethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl)-3-methyl-5-oxo-1-triethylsilanyloxy-oct-7-enyl]-8,10-dimethyl-3-triethylsilanyloxy-1-oxa-6-aza-spiro[4.5]decane-6-carboxylic acid propyl ester

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Chemical Property of (2R,3R,5S,8R,10S)-2-[(1R,3S)-7-((2S,3S,5R,6S)-3,5-Dimethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl)-3-methyl-5-oxo-1-triethylsilanyloxy-oct-7-enyl]-8,10-dimethyl-3-triethylsilanyloxy-1-oxa-6-aza-spiro[4.5]decane-6-carboxylic acid propyl ester

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Technology Process of (2R,3R,5S,8R,10S)-2-[(1R,3S)-7-((2S,3S,5R,6S)-3,5-Dimethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl)-3-methyl-5-oxo-1-triethylsilanyloxy-oct-7-enyl]-8,10-dimethyl-3-triethylsilanyloxy-1-oxa-6-aza-spiro[4.5]decane-6-carboxylic acid propyl ester

There total 11 articles about (2R,3R,5S,8R,10S)-2-[(1R,3S)-7-((2S,3S,5R,6S)-3,5-Dimethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl)-3-methyl-5-oxo-1-triethylsilanyloxy-oct-7-enyl]-8,10-dimethyl-3-triethylsilanyloxy-1-oxa-6-aza-spiro[4.5]decane-6-carboxylic acid propyl 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: 85.0%

: 910789-55-8
(2R,3R,5S,8R,10S)-2-[(1R,3R)-7-((2S,3S,5R,6S)-3,5-Dimethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl)-5-hydroxy-3-methyl-1-triethylsilanyloxy-oct-7-enyl]-8,10-dimethyl-3-triethylsilanyloxy-1-oxa-6-aza-spiro[4.5]decane-6-carboxylic acid propyl ester

: 910789-69-4
(2R,3R,5S,8R,10S)-2-[(1R,3S)-7-((2S,3S,5R,6S)-3,5-Dimethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl)-3-methyl-5-oxo-1-triethylsilanyloxy-oct-7-enyl]-8,10-dimethyl-3-triethylsilanyloxy-1-oxa-6-aza-spiro[4.5]decane-6-carboxylic acid propyl ester

Guidance literature:: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 20 ℃; for 3.5h;
DOI:10.1021/ol0613766

Reference yield:

: ((2R,4S,7R,8R,9R,11R)-7,9,13-Tris-benzyloxy-8-hydroxy-2,4,11-trimethyl-5-oxo-tridecyl)-carbamic acid allyl ester

: 910789-69-4
(2R,3R,5S,8R,10S)-2-[(1R,3S)-7-((2S,3S,5R,6S)-3,5-Dimethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl)-3-methyl-5-oxo-1-triethylsilanyloxy-oct-7-enyl]-8,10-dimethyl-3-triethylsilanyloxy-1-oxa-6-aza-spiro[4.5]decane-6-carboxylic acid propyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 184.7 mg / PPTS / 0.5 h / 20 °C

2: 91 percent / H₂ / Pd/C / methanol / 0.17 h / 20 °C / atmospheric pressure

3: 78 percent / Yb(OTf)3 / CH₂Cl₂ / 1 h / 0 °C

4: 96 percent / LDBB; di-tert-butylbiphenyl; Li / tetrahydrofuran / 0.42 h / -78 °C

5: 96 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / -40 °C

6: 89 percent / TBAF; acetic acid / tetrahydrofuran / 18 h / 0 °C

7: 87 percent / N-methylmorpholine N-oxide; molecular sieves 4 Angstroem; tetrapropylammonium perruthenate / CH₂Cl₂ / 0.5 h / 20 °C

8: 88 percent / InCl₃ / tetrahydrofuran / 0.5 h / 20 °C

9: 85 percent / IBX / dimethylsulfoxide / 3.5 h / 20 °C

With 2,6-dimethylpyridine; indium(III) chloride; tetrapropylammonium perruthennate; lithium 4,4′-di(tert-butyl)biphenyl; di(tert-butyl)-biphenyl; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; lithium; acetic acid; 4-methylmorpholine N-oxide; ytterbium(III) triflate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/ol0613766

Reference yield:

: {(2R,4S)-4-[(4R,5R)-4-Benzyloxy-5-((1R,3R)-1,5-bis-benzyloxy-3-methyl-pentyl)-2-methoxy-tetrahydro-furan-2-yl]-2-methyl-pentyl}-carbamic acid allyl ester

: 910789-69-4
(2R,3R,5S,8R,10S)-2-[(1R,3S)-7-((2S,3S,5R,6S)-3,5-Dimethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl)-3-methyl-5-oxo-1-triethylsilanyloxy-oct-7-enyl]-8,10-dimethyl-3-triethylsilanyloxy-1-oxa-6-aza-spiro[4.5]decane-6-carboxylic acid propyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 91 percent / H₂ / Pd/C / methanol / 0.17 h / 20 °C / atmospheric pressure

2: 78 percent / Yb(OTf)3 / CH₂Cl₂ / 1 h / 0 °C

3: 96 percent / LDBB; di-tert-butylbiphenyl; Li / tetrahydrofuran / 0.42 h / -78 °C

4: 96 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / -40 °C

5: 89 percent / TBAF; acetic acid / tetrahydrofuran / 18 h / 0 °C

6: 87 percent / N-methylmorpholine N-oxide; molecular sieves 4 Angstroem; tetrapropylammonium perruthenate / CH₂Cl₂ / 0.5 h / 20 °C

7: 88 percent / InCl₃ / tetrahydrofuran / 0.5 h / 20 °C

8: 85 percent / IBX / dimethylsulfoxide / 3.5 h / 20 °C

With 2,6-dimethylpyridine; indium(III) chloride; tetrapropylammonium perruthennate; lithium 4,4′-di(tert-butyl)biphenyl; di(tert-butyl)-biphenyl; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; lithium; acetic acid; 4-methylmorpholine N-oxide; ytterbium(III) triflate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/ol0613766