(S)-3-{(4S,5S,6S)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-butyric acid

Base Information

Chemical Name:(S)-3-{(4S,5S,6S)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-butyric acid
CAS No.:115047-26-2
Molecular Formula:C₃₀H₄₄O₅Si
Molecular Weight:512.762
Hs Code.:

Synonyms:(S)-3-{(4S,5S,6S)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-butyric acid

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Chemical Property of (S)-3-{(4S,5S,6S)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-butyric acid

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Technology Process of (S)-3-{(4S,5S,6S)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-butyric acid

There total 11 articles about (S)-3-{(4S,5S,6S)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-butyric 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:

: 112452-64-9
6(S)-(1(S)-methyl-2-cyanoethyl)-4(S)-<1(S)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-2,2,5(S)-trimethyl-1,3-dioxane

: 115047-26-2
(S)-3-{(4S,5S,6S)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-butyric acid

Guidance literature:: With potassium hydroxide; In diethylene glycol; at 200 ℃; for 40h;
DOI:10.1021/ja00224a032

Reference yield:

: Toluene-4-sulfonic acid (S)-2-{(4S,5R,6S)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propyl ester

: 115047-26-2
(S)-3-{(4S,5S,6S)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-butyric acid

Guidance literature:: Multi-step reaction with 2 steps

1: 14 mg / dimethylsulfoxide / 24 h / 80 °C

2: 55 mg / KOH / bis-(2-hydroxy-ethyl) ether / 40 h / 200 °C

With potassium hydroxide; In dimethyl sulfoxide; diethylene glycol;
DOI:10.1021/ja00224a032

Reference yield:

: 103576-61-0
4(S)-methyl-5(R)-<1(S)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-dihydro-2(3H)furanone

: 115047-26-2
(S)-3-{(4S,5S,6S)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-butyric acid

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) LDA / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, HMPA, -78 deg C, 3 h

2: 1.) NaH, 2.) (Ph₃P)4Pd, Ph₃P / 1.) THF, 25 deg C, 2.) THF, 0 deg C, 1 h, 25 deg C, 2 h

3: 71 percent / LiCl / H₂O; dimethylsulfoxide / 3 h / 200 °C

4: diethyl ether / 15 h / -18 °C

5: H₂O₂, HOAc / tetrahydrofuran / 0 deg C, 30 min, 25 deg C, 16 h

6: 1.)triethylamine, 4-(dimethylamino)pyridine, acetic anhydride, 2.) diisobutylaluminum hydride / 1.) CH₂Cl₂, 0 deg C, 30 min, 25 deg C, 1 h, reflux, 6 h, 2.) CH₂Sl₂, -78 deg C, 2 h

7: 93 mg / p-TsOH / 4 h / 25 °C

9: pyridine / 18 h / -6 °C

10: 14 mg / dimethylsulfoxide / 24 h / 80 °C

11: 55 mg / KOH / bis-(2-hydroxy-ethyl) ether / 40 h / 200 °C

With pyridine; dmap; potassium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dihydrogen peroxide; acetic anhydride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; triphenylphosphine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; water; dimethyl sulfoxide; diethylene glycol;
DOI:10.1021/ja00224a032