(R)-2-[(2S,4S,5R,6S)-6-((S)-2-{(R)-2-[(1S,2R,3S,4S,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-3,5-dihydroxy-2,4-dimethyl-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,4S,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-3,5-dihydroxy-2,4-dimethyl-hexyl]-oxiranyl}-1-methyl-ethyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionic acid
CAS No.:183960-71-6
Molecular Formula:C₃₃H₅₆O₈Si
Molecular Weight:608.888
Hs Code.:

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

There total 5 articles about (R)-2-[(2S,4S,5R,6S)-6-((S)-2-{(R)-2-[(1S,2R,3S,4S,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-3,5-dihydroxy-2,4-dimethyl-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: 70.0%

: (2S,4S,5R,6S)-6-((1S)-2-{(2R)-2-[(1S,2R,3S,4R,5R)-1-(tert-butyldimethylsiloxy)-3-hydroxy-2,4-dimethyl-5-(triisopropylsiloxy)hexyl]oxiranyl}-1-methylethyl)-4-((1R)-1-carboxyeth-1-yl)-5-methyl-2-phenyl-m-dioxane triethylamine complex

: 183960-71-6
(R)-2-[(2S,4S,5R,6S)-6-((S)-2-{(R)-2-[(1S,2R,3S,4S,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-3,5-dihydroxy-2,4-dimethyl-hexyl]-oxiranyl}-1-methyl-ethyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionic acid

Guidance literature:: With triethylamine hydrofluoride; In tetrahydrofuran; Ambient temperature;
DOI:10.1021/ja9806128

Reference yield:

: 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

: 183960-71-6
(R)-2-[(2S,4S,5R,6S)-6-((S)-2-{(R)-2-[(1S,2R,3S,4S,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-3,5-dihydroxy-2,4-dimethyl-hexyl]-oxiranyl}-1-methyl-ethyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionic acid

Guidance literature:: With triethylamine hydrofluoride; at 25 ℃; Yield given;
DOI:10.1021/ja963002l

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 183960-71-6
(R)-2-[(2S,4S,5R,6S)-6-((S)-2-{(R)-2-[(1S,2R,3S,4S,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-3,5-dihydroxy-2,4-dimethyl-hexyl]-oxiranyl}-1-methyl-ethyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 2,6-lutidine / -78 °C

2: LiOOH / 0 °C

3: Et₃N*HF / 25 °C

With 2,6-dimethylpyridine; lithium hydroperoxide; triethylamine hydrofluoride;
DOI:10.1021/ja963002l