(4R,5S)-3-{(E)-(2R,3S,6S)-6-[(2R,3S,5S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-5-methyl-tetrahydro-pyran-2-yl]-3-hydroxy-2-methoxy-4-methyl-hept-4-enoyl}-4-methyl-5-phenyl-oxazolidin-2-one

Base Information

Chemical Name:(4R,5S)-3-{(E)-(2R,3S,6S)-6-[(2R,3S,5S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-5-methyl-tetrahydro-pyran-2-yl]-3-hydroxy-2-methoxy-4-methyl-hept-4-enoyl}-4-methyl-5-phenyl-oxazolidin-2-one
CAS No.:175356-50-0
Molecular Formula:C₃₂H₅₁NO₈Si
Molecular Weight:605.844
Hs Code.:

(4R,5S)-3-{(E)-(2R,3S,6S)-6-[(2R,3S,5S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-5-methyl-tetrahydro-pyran-2-yl]-3-hydroxy-2-methoxy-4-methyl-hept-4-enoyl}-4-methyl-5-phenyl-oxazolidin-2-one

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Chemical Property of (4R,5S)-3-{(E)-(2R,3S,6S)-6-[(2R,3S,5S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-5-methyl-tetrahydro-pyran-2-yl]-3-hydroxy-2-methoxy-4-methyl-hept-4-enoyl}-4-methyl-5-phenyl-oxazolidin-2-one

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Technology Process of (4R,5S)-3-{(E)-(2R,3S,6S)-6-[(2R,3S,5S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-5-methyl-tetrahydro-pyran-2-yl]-3-hydroxy-2-methoxy-4-methyl-hept-4-enoyl}-4-methyl-5-phenyl-oxazolidin-2-one

There total 16 articles about (4R,5S)-3-{(E)-(2R,3S,6S)-6-[(2R,3S,5S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-5-methyl-tetrahydro-pyran-2-yl]-3-hydroxy-2-methoxy-4-methyl-hept-4-enoyl}-4-methyl-5-phenyl-oxazolidin-2-one 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:

: 95481-54-2
<4R-<4α(2R^*,3R^*),5α>>-3-<3-(2-furanyl)-3-hydroxy-2-methyl-1-oxopropyl>-4-methyl-5-phenyl-2-oxazolidinone

: 175356-50-0
(4R,5S)-3-{(E)-(2R,3S,6S)-6-[(2R,3S,5S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-5-methyl-tetrahydro-pyran-2-yl]-3-hydroxy-2-methoxy-4-methyl-hept-4-enoyl}-4-methyl-5-phenyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 14 steps

1: 95 percent / Br₂, H₂O / acetonitrile / 1 h / -20 °C

2: 51 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -20 °C

3: 1.) copper iodide, 2.) chlorotrimethylsilane / 1.) Et₂O, THF, 0 deg C, 20 min, 2.) Et₂O, THF, -78 deg C, 30 min

4: 1.) NaBH₄, 2.) camphorsulfonic acid / 1.) EtOH, THF, -20 deg C, 1.5 h, 2.) EtOH, THF, -20 deg C, 15 min

5: 80 percent / DIBAL-H / hexane; tetrahydrofuran / 1 h / 0 °C

6: 73 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 22 h / Ambient temperature

7: 80 percent / diethylazodicarboxylate, Ph₃P / benzene / 20 h / Ambient temperature

8: 99 percent / NaOH / methanol; tetrahydrofuran / 0.25 h / Ambient temperature

9: 1.) KH / 1.) THF, 0 deg C, 15 min, 2.) THF, 0 deg C, 20 min

10: 99 percent / aq. trifluoroacetic acid / tetrahydrofuran / 2 h / 0 °C

11: 87 percent / tetrapropylammonium perruthenate (VII), 4-methylmorpholine N-oxide monohydrate, 4A molecular sieves / CH₂Cl₂; acetonitrile / 0.75 h / Ambient temperature

12: 1.) s-BuLi / 1.) cyclohexane, THF, -78 deg C, 0.5 h, 2.) cyclohexane, THF, -20 deg C, 1 h

13: trifluoroacetic acid / tetrahydrofuran / 1 h / 0 °C

14: 1.) di-n-butylborontriflate, Et₃N, 3.) NaHPO₄ buffer, 30percent hydrogen peroxide

With 2,6-dimethylpyridine; dmap; sodium hydroxide; sodium tetrahydroborate; copper(l) iodide; chloro-trimethyl-silane; tetrapropylammonium perruthennate; 4 A molecular sieve; NaHPO₄ buffer; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; water; dihydrogen peroxide; bromine; sec.-butyllithium; potassium hydride; diisobutylaluminium hydride; 4-methylmorpholine 4-oxide monohydrate; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile; benzene;
DOI:10.1016/0040-4020(95)01107-2

Reference yield:

: (4R,5S)-3-[(R)-2-((R)-6-Hydroxy-3-oxo-3,6-dihydro-2H-pyran-2-yl)-propionyl]-4-methyl-5-phenyl-oxazolidin-2-one

: 175356-50-0
(4R,5S)-3-{(E)-(2R,3S,6S)-6-[(2R,3S,5S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-5-methyl-tetrahydro-pyran-2-yl]-3-hydroxy-2-methoxy-4-methyl-hept-4-enoyl}-4-methyl-5-phenyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 13 steps

1: 51 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -20 °C

2: 1.) copper iodide, 2.) chlorotrimethylsilane / 1.) Et₂O, THF, 0 deg C, 20 min, 2.) Et₂O, THF, -78 deg C, 30 min

3: 1.) NaBH₄, 2.) camphorsulfonic acid / 1.) EtOH, THF, -20 deg C, 1.5 h, 2.) EtOH, THF, -20 deg C, 15 min

4: 80 percent / DIBAL-H / hexane; tetrahydrofuran / 1 h / 0 °C

5: 73 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 22 h / Ambient temperature

6: 80 percent / diethylazodicarboxylate, Ph₃P / benzene / 20 h / Ambient temperature

7: 99 percent / NaOH / methanol; tetrahydrofuran / 0.25 h / Ambient temperature

8: 1.) KH / 1.) THF, 0 deg C, 15 min, 2.) THF, 0 deg C, 20 min

9: 99 percent / aq. trifluoroacetic acid / tetrahydrofuran / 2 h / 0 °C

10: 87 percent / tetrapropylammonium perruthenate (VII), 4-methylmorpholine N-oxide monohydrate, 4A molecular sieves / CH₂Cl₂; acetonitrile / 0.75 h / Ambient temperature

11: 1.) s-BuLi / 1.) cyclohexane, THF, -78 deg C, 0.5 h, 2.) cyclohexane, THF, -20 deg C, 1 h

12: trifluoroacetic acid / tetrahydrofuran / 1 h / 0 °C

13: 1.) di-n-butylborontriflate, Et₃N, 3.) NaHPO₄ buffer, 30percent hydrogen peroxide

With 2,6-dimethylpyridine; dmap; sodium hydroxide; sodium tetrahydroborate; copper(l) iodide; chloro-trimethyl-silane; tetrapropylammonium perruthennate; 4 A molecular sieve; NaHPO₄ buffer; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; dihydrogen peroxide; sec.-butyllithium; potassium hydride; diisobutylaluminium hydride; 4-methylmorpholine 4-oxide monohydrate; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile; benzene;
DOI:10.1016/0040-4020(95)01107-2

Reference yield:

: 136113-80-9
O-tert-butyldimethylsilyl-2,6-dimethyl-7-O-(tert-butyldimethylsilyl)-2,3,6-trideoxy-β-L-gulo-heptopyranoside

: 175356-50-0
(4R,5S)-3-{(E)-(2R,3S,6S)-6-[(2R,3S,5S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-5-methyl-tetrahydro-pyran-2-yl]-3-hydroxy-2-methoxy-4-methyl-hept-4-enoyl}-4-methyl-5-phenyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: 80 percent / diethylazodicarboxylate, Ph₃P / benzene / 20 h / Ambient temperature

2: 99 percent / NaOH / methanol; tetrahydrofuran / 0.25 h / Ambient temperature

3: 1.) KH / 1.) THF, 0 deg C, 15 min, 2.) THF, 0 deg C, 20 min

4: 99 percent / aq. trifluoroacetic acid / tetrahydrofuran / 2 h / 0 °C

5: 87 percent / tetrapropylammonium perruthenate (VII), 4-methylmorpholine N-oxide monohydrate, 4A molecular sieves / CH₂Cl₂; acetonitrile / 0.75 h / Ambient temperature

6: 1.) s-BuLi / 1.) cyclohexane, THF, -78 deg C, 0.5 h, 2.) cyclohexane, THF, -20 deg C, 1 h

7: trifluoroacetic acid / tetrahydrofuran / 1 h / 0 °C

8: 1.) di-n-butylborontriflate, Et₃N, 3.) NaHPO₄ buffer, 30percent hydrogen peroxide

With sodium hydroxide; tetrapropylammonium perruthennate; 4 A molecular sieve; NaHPO₄ buffer; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; sec.-butyllithium; potassium hydride; 4-methylmorpholine 4-oxide monohydrate; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; benzene;
DOI:10.1016/0040-4020(95)01107-2