(S)-7-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-2-yn-1-ol

Base Information

• Chemical Name: (S)-7-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-2-yn-1-ol
• CAS No.: 452920-21-7
• Molecular Formula: C₂₈H₃₈O₄Si
• Molecular Weight: 466.693
• Mol file: 452920-21-7.mol

Synonyms:(S)-7-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-2-yn-1-ol

Chemical Property of (S)-7-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-2-yn-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-7-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-2-yn-1-ol

There total 1 articles about (S)-7-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-2-yn-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:

2,3-isopropylidene-glyceraldehyde (15186-48-8) + 6-(tert-butyldiphenylsilyloxy)hexyne lithium → (S)-7-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-2-yn-1-ol (452920-21-7) + (R)-7-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-2-yn-1-ol (452920-23-9)

Guidance literature:

6-(tert-butyldiphenylsilyloxy)hexyne lithium; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h;

2,3-isopropylidene-glyceraldehyde; In tetrahydrofuran; at -78 - 20 ℃; for 5h;

DOI:10.1016/S0040-4039(02)00699-8

Reference yield: 88.0%

benzoic acid (65-85-0,8013-63-6) + (S)-7-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-2-yn-1-ol (452920-21-7) → Benzoic acid (R)-7-(tert-butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-2-ynyl ester (452920-22-8)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In benzene; at 23 ℃; for 12h;

DOI:10.1016/S0040-4039(02)00699-8

Reference yield:

(S)-7-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-2-yn-1-ol (452920-21-7) → Toluene-4-sulfonic acid (S)-2-hydroxy-2-[(1S,2S)-2-((R)-6-oxo-tetrahydro-pyran-2-yl)-cyclopropyl]-ethyl ester

Guidance literature:

Multi-step reaction with 11 steps

1: 88 percent / PPh₃; DEAD / benzene / 12 h / 23 °C

2: 92 percent / NaOH / methanol / 12 h / 23 °C

3: PPh₃; DEAD / benzene / 3 h / 23 °C

4: CrSO₄; H₂O / dimethylformamide / 2 h / 23 °C

5: n-Bu₄NF / tetrahydrofuran / 18 h / 23 °C

6: PDC / dimethylformamide / 40 h / 23 °C

7: NaH; I₂ / tetrahydrofuran

8: HgCl₂ / Mg / tetrahydrofuran; H₂O / 12 h / 23 °C

9: PPh₃; DEAD / benzene / 7 h / 23 °C

10: CF₃CO₂H / tetrahydrofuran; H₂O / 10 h / 40 °C

11: py / 36 h / 4 °C

With pyridine; sodium hydroxide; dipyridinium dichromate; chromium sulfate; tetrabutyl ammonium fluoride; water; iodine; sodium hydride; triphenylphosphine; trifluoroacetic acid; mercury dichloride; diethylazodicarboxylate; magnesium; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; benzene; 1: Mitsunobu inversion / 9: Mitsunobu inversion;

DOI:10.1016/S0040-4039(02)00699-8

upstream raw materials:

2,3-isopropylidene-glyceraldehyde

Downstream raw materials:

Benzoic acid (R)-7-(tert-butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-2-ynyl ester

(R)-7-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-2-yn-1-ol

(S)-6-[(1S,3S)-2,2-Bis-benzenesulfonyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-cyclopropyl]-tetrahydro-pyran-2-one

(E)-(S)-8,8-Bis-benzenesulfonyl-7-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-oct-5-enoic acid