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

Base Information

Chemical Name:(2S,3S,4R)-4-{(4S,5S,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-2-methyl-pentane-1,3-diol
CAS No.:81470-90-8
Molecular Formula:C₃₂H₅₀O₅Si
Molecular Weight:542.832
Hs Code.:

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

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

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

There total 22 articles about (2S,3S,4R)-4-{(4S,5S,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-2-methyl-pentane-1,3-diol 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: 96.0%

: 917-54-4
methyllithium

: 81470-89-5
[(2R,3R)-3-((S)-1-{(4R,5S,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-ethyl)-oxiranyl]-methanol

: 81470-90-8
(2S,3S,4R)-4-{(4S,5S,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-2-methyl-pentane-1,3-diol

Guidance literature:: With copper(l) iodide; In diethyl ether; -40 deg C, 5 h. then -23 deg C, 30 min.;
DOI:10.1016/S0040-4020(01)93261-2

Reference yield:

: 81470-77-1,98102-72-8,100760-30-3,115181-74-3,133006-91-4,135211-99-3,138124-14-8,145514-09-6
(2S,3R,4R)-1-(benzyloxy)-3,5-(isopropylidenedioxy)-2,4-dimethylpentane

: 81470-90-8
(2S,3S,4R)-4-{(4S,5S,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-2-methyl-pentane-1,3-diol

Guidance literature:: Multi-step reaction with 13 steps

1: 96 percent / liquid ammonia, Li / tetrahydrofuran / 0.33 h / Heating

2: oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 0.25 h / -78 °C

3: 86 percent / chromic chloride, LAH / tetrahydrofuran / 0.5 h

5: 100 percent / AcOH / H₂O / 0.17 h / 40 °C

6: 92 percent / pyridine / CH₂Cl₂ / 0 deg C, 1.5 h. then room temp., 2 h.

7: 99 percent / camphorsulfonic acid / 2 h / Ambient temperature

8: 100 percent / LAH / diethyl ether / 0.25 h / 25 °C

9: oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 0.25 h / -78 °C

10: t-BuOK / tetrahydrofuran / 0.33 h / -78 °C

11: DIBAL / CH₂Cl₂; hexane / 0.67 h

12: titanium tetraisopropoxide, t-butyl hydroperoxide / L(+)-diethyl tartrate / CH₂Cl₂ / 0.67 h / -23 °C

13: 96 percent / copper (I) iodide / diethyl ether / -40 deg C, 5 h. then -23 deg C, 30 min.

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; copper(l) iodide; lithium aluminium tetrahydride; oxalyl dichloride; camphor-10-sulfonic acid; potassium tert-butylate; ammonia; chromium(III) chloride; lithium; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; diethyl (2R,3R)-tartrate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water;
DOI:10.1016/S0040-4020(01)93261-2

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 81470-90-8
(2S,3S,4R)-4-{(4S,5S,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-2-methyl-pentane-1,3-diol

Guidance literature:: Multi-step reaction with 10 steps

1: 99.6 percent / imidazol / dimethylformamide / 0.5 h / Ambient temperature

2: 100 percent / AcOH / H₂O / 0.17 h / 40 °C

3: 92 percent / pyridine / CH₂Cl₂ / 0 deg C, 1.5 h. then room temp., 2 h.

4: 99 percent / camphorsulfonic acid / 2 h / Ambient temperature

5: 100 percent / LAH / diethyl ether / 0.25 h / 25 °C

6: oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 0.25 h / -78 °C

7: t-BuOK / tetrahydrofuran / 0.33 h / -78 °C

8: DIBAL / CH₂Cl₂; hexane / 0.67 h

9: titanium tetraisopropoxide, t-butyl hydroperoxide / L(+)-diethyl tartrate / CH₂Cl₂ / 0.67 h / -23 °C

10: 96 percent / copper (I) iodide / diethyl ether / -40 deg C, 5 h. then -23 deg C, 30 min.

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; copper(l) iodide; lithium aluminium tetrahydride; oxalyl dichloride; camphor-10-sulfonic acid; potassium tert-butylate; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; diethyl (2R,3R)-tartrate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)93261-2