(R)-4-Benzyl-3-{(R)-2-[(2S,4S,5R,6S)-6-((1S,4R,5S,6R,7R,8R)-6-benzyloxy-4-hydroxy-1,5,7-trimethyl-3-methylene-8-triisopropylsilanyloxy-nonyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionyl}-oxazolidin-2-one

Base Information

Chemical Name:(R)-4-Benzyl-3-{(R)-2-[(2S,4S,5R,6S)-6-((1S,4R,5S,6R,7R,8R)-6-benzyloxy-4-hydroxy-1,5,7-trimethyl-3-methylene-8-triisopropylsilanyloxy-nonyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionyl}-oxazolidin-2-one
CAS No.:183960-86-3
Molecular Formula:C₅₃H₇₇NO₈Si
Molecular Weight:884.282
Hs Code.:

(R)-4-Benzyl-3-{(R)-2-[(2S,4S,5R,6S)-6-((1S,4R,5S,6R,7R,8R)-6-benzyloxy-4-hydroxy-1,5,7-trimethyl-3-methylene-8-triisopropylsilanyloxy-nonyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionyl}-oxazolidin-2-one

Synonyms:(R)-4-Benzyl-3-{(R)-2-[(2S,4S,5R,6S)-6-((1S,4R,5S,6R,7R,8R)-6-benzyloxy-4-hydroxy-1,5,7-trimethyl-3-methylene-8-triisopropylsilanyloxy-nonyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionyl}-oxazolidin-2-one

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Chemical Property of (R)-4-Benzyl-3-{(R)-2-[(2S,4S,5R,6S)-6-((1S,4R,5S,6R,7R,8R)-6-benzyloxy-4-hydroxy-1,5,7-trimethyl-3-methylene-8-triisopropylsilanyloxy-nonyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionyl}-oxazolidin-2-one

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Technology Process of (R)-4-Benzyl-3-{(R)-2-[(2S,4S,5R,6S)-6-((1S,4R,5S,6R,7R,8R)-6-benzyloxy-4-hydroxy-1,5,7-trimethyl-3-methylene-8-triisopropylsilanyloxy-nonyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionyl}-oxazolidin-2-one

There total 9 articles about (R)-4-Benzyl-3-{(R)-2-[(2S,4S,5R,6S)-6-((1S,4R,5S,6R,7R,8R)-6-benzyloxy-4-hydroxy-1,5,7-trimethyl-3-methylene-8-triisopropylsilanyloxy-nonyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionyl}-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: 61.0%

: 183960-84-1
(R)-4-Benzyl-3-{(R)-2-[(2S,4S,5R,6S)-6-((1S,5R,6S,7R,8R)-6-benzyloxy-1,5,7-trimethyl-3-methylene-4-oxo-8-triisopropylsilanyloxy-nonyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionyl}-oxazolidin-2-one

: (R)-4-Benzyl-3-{(R)-2-[(2S,4S,5R,6S)-6-((1S,4S,5S,6R,7R,8R)-6-benzyloxy-4-hydroxy-1,5,7-trimethyl-3-methylene-8-triisopropylsilanyloxy-nonyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionyl}-oxazolidin-2-one

: 183960-86-3
(R)-4-Benzyl-3-{(R)-2-[(2S,4S,5R,6S)-6-((1S,4R,5S,6R,7R,8R)-6-benzyloxy-4-hydroxy-1,5,7-trimethyl-3-methylene-8-triisopropylsilanyloxy-nonyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionyl}-oxazolidin-2-one

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; In tetrahydrofuran; methanol; at -78 ℃; for 8h;
DOI:10.1021/ja9806128

Reference yield:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 183960-86-3
(R)-4-Benzyl-3-{(R)-2-[(2S,4S,5R,6S)-6-((1S,4R,5S,6R,7R,8R)-6-benzyloxy-4-hydroxy-1,5,7-trimethyl-3-methylene-8-triisopropylsilanyloxy-nonyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionyl}-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 73 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -5 °C

2: 84 percent / TfOH / CH₂Cl₂; diethyl ether / 3 h / Ambient temperature

3: 94 percent / 30percent aq. H₂O₂, 0.2 M aq. LiOH / tetrahydrofuran / 6 h / 0 °C

4: (COCl)2, DMF / benzene / 4 h / Ambient temperature

5: 85 percent / Pd₂(dba)3, i-Pr₂NEt / benzene / 1.5 h / Ambient temperature

6: 61 percent / NaBH₄, CeCl₃*7H₂O / methanol; tetrahydrofuran / 8 h / -78 °C

With 2,6-dimethylpyridine; lithium hydroxide; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; trifluorormethanesulfonic acid; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzene;
DOI:10.1021/ja9806128

Reference yield:

: 101712-01-0,141423-22-5,141423-21-4
(R)-1-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-methylpentane-1,3-dione

: 183960-86-3
(R)-4-Benzyl-3-{(R)-2-[(2S,4S,5R,6S)-6-((1S,4R,5S,6R,7R,8R)-6-benzyloxy-4-hydroxy-1,5,7-trimethyl-3-methylene-8-triisopropylsilanyloxy-nonyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionyl}-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) Sn(OTf)2, Et₃N / 1.) CH₂Cl₂, -20 deg C, 1 h, 2.) CH₂Cl₂, -78 deg C, 30 min

2: 100 percent / NaBH₄, AcOH / 0.25 h / Ambient temperature

3: 73 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -5 °C

4: 84 percent / TfOH / CH₂Cl₂; diethyl ether / 3 h / Ambient temperature

5: 94 percent / 30percent aq. H₂O₂, 0.2 M aq. LiOH / tetrahydrofuran / 6 h / 0 °C

6: (COCl)2, DMF / benzene / 4 h / Ambient temperature

7: 85 percent / Pd₂(dba)3, i-Pr₂NEt / benzene / 1.5 h / Ambient temperature

8: 61 percent / NaBH₄, CeCl₃*7H₂O / methanol; tetrahydrofuran / 8 h / -78 °C

With 2,6-dimethylpyridine; lithium hydroxide; sodium tetrahydroborate; tin(II) trifluoromethanesulfonate; cerium(III) chloride; oxalyl dichloride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; trifluorormethanesulfonic acid; dihydrogen peroxide; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzene;
DOI:10.1021/ja9806128