(R)-2-[(2S,4S,5R,6S)-6-((S)-2-{(R)-2-[(1S,2R,3S,4R,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-hexyl]-oxiranyl}-1-methyl-ethyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionic acid

Base Information

Chemical Name:(R)-2-[(2S,4S,5R,6S)-6-((S)-2-{(R)-2-[(1S,2R,3S,4R,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-hexyl]-oxiranyl}-1-methyl-ethyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionic acid
CAS No.:211187-44-9
Molecular Formula:C₄₂H₇₆O₈Si₂
Molecular Weight:765.232
Hs Code.:

(R)-2-[(2S,4S,5R,6S)-6-((S)-2-{(R)-2-[(1S,2R,3S,4R,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-hexyl]-oxiranyl}-1-methyl-ethyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionic acid

Synonyms:(R)-2-[(2S,4S,5R,6S)-6-((S)-2-{(R)-2-[(1S,2R,3S,4R,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-hexyl]-oxiranyl}-1-methyl-ethyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionic acid

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Chemical Property of (R)-2-[(2S,4S,5R,6S)-6-((S)-2-{(R)-2-[(1S,2R,3S,4R,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-hexyl]-oxiranyl}-1-methyl-ethyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionic acid

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Technology Process of (R)-2-[(2S,4S,5R,6S)-6-((S)-2-{(R)-2-[(1S,2R,3S,4R,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-hexyl]-oxiranyl}-1-methyl-ethyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionic acid

There total 14 articles about (R)-2-[(2S,4S,5R,6S)-6-((S)-2-{(R)-2-[(1S,2R,3S,4R,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-hexyl]-oxiranyl}-1-methyl-ethyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionic acid 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: 92.0%

: 211187-42-7
(R)-4-Benzyl-3-{(R)-2-[(2S,4S,5R,6S)-6-((S)-2-{(R)-2-[(1S,2R,3S,4R,5R)-1-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-hexyl]-oxiranyl}-1-methyl-ethyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionyl}-oxazolidin-2-one

: 211187-44-9
(R)-2-[(2S,4S,5R,6S)-6-((S)-2-{(R)-2-[(1S,2R,3S,4R,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-hexyl]-oxiranyl}-1-methyl-ethyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionic acid

Guidance literature:: With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 0 ℃; for 60h;
DOI:10.1021/ja9806128

Reference yield:

: 211187-40-5
(R)-4-Benzyl-3-[(R)-2-((2S,4S,5R,6S)-6-{(S)-2-[(R)-2-((1S,2R,3R,4R,5R)-1,3-dihydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-hexyl)-oxiranyl]-1-methyl-ethyl}-5-methyl-2-phenyl-[1,3]dioxan-4-yl)-propionyl]-oxazolidin-2-one

: 211187-44-9
(R)-2-[(2S,4S,5R,6S)-6-((S)-2-{(R)-2-[(1S,2R,3S,4R,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-hexyl]-oxiranyl}-1-methyl-ethyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 83 percent / 2,6-lutidine / CH₂Cl₂ / 19 h / -78 °C

2: 92 percent / 30percent aq. H₂O₂, 0.2 M aq. LiOH / tetrahydrofuran / 60 h / 0 °C

With 2,6-dimethylpyridine; lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja9806128

Reference yield:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 211187-44-9
(R)-2-[(2S,4S,5R,6S)-6-((S)-2-{(R)-2-[(1S,2R,3S,4R,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-hexyl]-oxiranyl}-1-methyl-ethyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionic acid

Guidance literature:: Multi-step reaction with 10 steps

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

2: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.67 h / Ambient temperature

3: 98 percent / 30percent aq. H₂O₂, 0.2 M aq. LiOH / tetrahydrofuran / 48 h / 0 °C

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

5: Pd₂(dba)3, i-Pr₂NEt / benzene / 0.5 h / Ambient temperature

6: 95 percent / HF*pyridine / tetrahydrofuran / 2.5 h / 0 °C

7: 86 percent / Zn(BH₄)2 / CH₂Cl₂; diethyl ether / a) -50 deg C, 15.5 h, b) 0 deg C, 1 h

8: 1 percent / t-BuOOH, VO(acac)2 / benzene; decane / 0.75 h / Ambient temperature

9: 83 percent / 2,6-lutidine / CH₂Cl₂ / 19 h / -78 °C

10: 92 percent / 30percent aq. H₂O₂, 0.2 M aq. LiOH / tetrahydrofuran / 60 h / 0 °C

With 2,6-dimethylpyridine; tert.-butylhydroperoxide; lithium hydroxide; zinc(II) tetrahydroborate; oxalyl dichloride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; bis(acetylacetonate)oxovanadium; dihydrogen peroxide; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; In tetrahydrofuran; diethyl ether; decane; dichloromethane; benzene;
DOI:10.1021/ja9806128