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

Base Information

• Chemical Name: (R)-7-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-2-yn-1-ol
• CAS No.: 452920-23-9
• Molecular Formula: C₂₈H₃₈O₄Si
• Molecular Weight: 466.693
• Mol file: 452920-23-9.mol

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

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

There total 5 articles about (R)-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: 92.0%

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) → (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:

With sodium hydroxide; In methanol; at 23 ℃; for 12h;

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

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:

2,3-isopropylidene-glyceraldehyde (15186-48-8) → (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:

Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C

1.2: tetrahydrofuran / 5 h / -78 - 20 °C

2.1: 88 percent / PPh₃; DEAD / benzene / 12 h / 23 °C

3.1: 92 percent / NaOH / methanol / 12 h / 23 °C

With sodium hydroxide; n-butyllithium; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; benzene; 2.1: Mitsunobu inversion;

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

upstream raw materials:

2,3-isopropylidene-glyceraldehyde

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

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

Downstream raw materials:

(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

(R)-6-{(1S,2S)-2-[(2E,6Z)-(1R,4S)-1-Hydroxy-4-(4-methoxy-benzyloxy)-dodeca-2,6-dienyl]-cyclopropyl}-tetrahydro-pyran-2-one

[(S)-8,8-Bis-benzenesulfonyl-7-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-oct-5-ynyloxy]-tert-butyl-diphenyl-silane