[(2S,3S)-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

Base Information

• Chemical Name: [(2S,3S)-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
• CAS No.: 81470-89-5
• Molecular Formula: C₃₁H₄₆O₅Si
• Molecular Weight: 526.789
• Mol file: 81470-89-5.mol

Synonyms:[(2S,3S)-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

Chemical Property of [(2S,3S)-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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2S,3S)-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

There total 42 articles about [(2S,3S)-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 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:

(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 (81470-88-4) → [(2S,3S)-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 (81470-89-5) + [(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 (81470-89-5)

Guidance literature:

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; In dichloromethane; at -23 ℃; for 0.666667h; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4020(01)93261-2

Reference yield:

(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 (81470-88-4) → [(2S,3S)-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 (81470-89-5) + [(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 (81470-89-5)

Guidance literature:

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; In dichloromethane; at -23 ℃; for 0.666667h; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4020(01)93261-2

Reference yield:

(2R,3R,4R)-5-(benzyloxy)-2,4-dimethyl-1,3-pentanediol (108393-30-2) → [(2S,3S)-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 (81470-89-5)

Guidance literature:

Multi-step reaction with 13 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

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

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; 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; acetone;

DOI:10.1016/S0040-4020(01)93261-2

upstream raw materials:

(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

(2E,4R)-5-(benzyloxy)-4-methyl-2-penten-1-ol

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

(2S,3R,4R)-1-(benzyloxy)-3,5-(isopropylidenedioxy)-2,4-dimethylpentane

Downstream raw materials:

(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

tert-Butyl-diphenyl-((R)-2-{(4S,5S,6S)-2,2,5-trimethyl-6-[(R)-1-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-ethyl]-[1,3]dioxan-4-yl}-propoxy)-silane