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

Base Information

Chemical Name:(E)-(R)-4-{(4S,5R,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pent-2-en-1-ol
CAS No.:81470-88-4
Molecular Formula:C₃₁H₄₆O₄Si
Molecular Weight:510.789
Hs Code.:

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

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

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

There total 20 articles about (E)-(R)-4-{(4S,5R,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pent-2-en-1-ol 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:

: 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

: 81470-88-4
(E)-(R)-4-{(4S,5R,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pent-2-en-1-ol

Guidance literature:: Multi-step reaction with 11 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

With pyridine; lithium aluminium tetrahydride; oxalyl dichloride; camphor-10-sulfonic acid; potassium tert-butylate; ammonia; chromium(III) chloride; lithium; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water;
DOI:10.1016/S0040-4020(01)93261-2

Reference yield:

: 81520-03-8
(2E,4R)-5-(benzyloxy)-4-methyl-2-penten-1-ol

: 81470-88-4
(E)-(R)-4-{(4S,5R,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pent-2-en-1-ol

Guidance literature:: Multi-step reaction with 14 steps

1: titanium tetraisopropoxide, t-butyl hydroperoxide / D(-)-diethyl tartrate / CH₂Cl₂ / 0.67 h / -23 °C

2: 89 percent / copper (I) iodide / diethyl ether / -40 deg C, 5 h. then -23 deg C, 30 min.

3: 92 percent / camphorsulfonic acid / acetone / 0.5 h / 25 °C

4: 96 percent / liquid ammonia, Li / tetrahydrofuran / 0.33 h / Heating

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

6: 86 percent / chromic chloride, LAH / tetrahydrofuran / 0.5 h

8: 100 percent / AcOH / H₂O / 0.17 h / 40 °C

9: 92 percent / pyridine / CH₂Cl₂ / 0 deg C, 1.5 h. then room temp., 2 h.

10: 99 percent / camphorsulfonic acid / 2 h / Ambient temperature

11: 100 percent / LAH / diethyl ether / 0.25 h / 25 °C

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

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

14: DIBAL / CH₂Cl₂; hexane / 0.67 h

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 (2S,3S)-tartrate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; acetone;
DOI:10.1016/S0040-4020(01)93261-2

Reference yield:

: 108393-30-2
(2R,3R,4R)-5-(benzyloxy)-2,4-dimethyl-1,3-pentanediol

: 81470-88-4
(E)-(R)-4-{(4S,5R,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pent-2-en-1-ol

Guidance literature:: Multi-step reaction with 12 steps

1: 92 percent / camphorsulfonic acid / acetone / 0.5 h / 25 °C

2: 96 percent / liquid ammonia, Li / tetrahydrofuran / 0.33 h / Heating

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

4: 86 percent / chromic chloride, LAH / tetrahydrofuran / 0.5 h

6: 100 percent / AcOH / H₂O / 0.17 h / 40 °C

7: 92 percent / pyridine / CH₂Cl₂ / 0 deg C, 1.5 h. then room temp., 2 h.

8: 99 percent / camphorsulfonic acid / 2 h / Ambient temperature

9: 100 percent / LAH / diethyl ether / 0.25 h / 25 °C

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

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

12: DIBAL / CH₂Cl₂; hexane / 0.67 h

With pyridine; lithium aluminium tetrahydride; oxalyl dichloride; camphor-10-sulfonic acid; potassium tert-butylate; ammonia; chromium(III) chloride; lithium; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; acetone;
DOI:10.1016/S0040-4020(01)93261-2