(2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-((E)-5-trimethylsilanyl-pent-2-en-4-ynyl)-tetrahydro-furan-3-ol

Base Information

• Chemical Name: (2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-((E)-5-trimethylsilanyl-pent-2-en-4-ynyl)-tetrahydro-furan-3-ol
• CAS No.: 168777-41-1
• Molecular Formula: C₂₉H₄₀O₃Si₂
• Molecular Weight: 492.806
• Mol file: 168777-41-1.mol

Synonyms:(2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-((E)-5-trimethylsilanyl-pent-2-en-4-ynyl)-tetrahydro-furan-3-ol

Chemical Property of (2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-((E)-5-trimethylsilanyl-pent-2-en-4-ynyl)-tetrahydro-furan-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-((E)-5-trimethylsilanyl-pent-2-en-4-ynyl)-tetrahydro-furan-3-ol

There total 7 articles about (2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-((E)-5-trimethylsilanyl-pent-2-en-4-ynyl)-tetrahydro-furan-3-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: 88.0%

(3aR,5R,6aR)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-hexahydro-furo[3,2-b]furan-2-ol + C23H24OPSi(1+)*Br(1-) → (2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-((Z)-5-trimethylsilanyl-pent-2-en-4-ynyl)-tetrahydro-furan-3-ol + (2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-((E)-5-trimethylsilanyl-pent-2-en-4-ynyl)-tetrahydro-furan-3-ol (168777-41-1)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; for 5h;

DOI:10.1016/00404-0399(50)1100V-

Reference yield: 8.0%

(3-trimethylsilyl-2-propynyl)triphenylphosphonium bromide (42134-49-6) + [(2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-furan-2-yl]-acetaldehyde (168777-40-0) → (2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-((Z)-5-trimethylsilanyl-pent-2-en-4-ynyl)-tetrahydro-furan-3-ol + (2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-((E)-5-trimethylsilanyl-pent-2-en-4-ynyl)-tetrahydro-furan-3-ol (168777-41-1)

Guidance literature:

With potassium tert-butylate; In diethyl ether; Ambient temperature;

DOI:10.1021/jo972066r

Reference yield:

methyl (3R)-4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate (159801-08-8) → (2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-((E)-5-trimethylsilanyl-pent-2-en-4-ynyl)-tetrahydro-furan-3-ol (168777-41-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 89 percent / AlMe₃ / CH₂Cl₂ / 40 °C

2: 53 percent / tetrahydrofuran / 20 - 50 °C

3: 89 percent / Me₄NH(OAc)3 / acetonitrile; acetic acid / -40 °C

4: 93 percent / PdCl₂, CuCl₂, AcONa / acetic acid / Ambient temperature

5: 100 percent / DIBAL-H / tetrahydrofuran / -78 °C

6: 85 percent / t-BuOK / diethyl ether / Ambient temperature

With potassium tert-butylate; trimethylaluminum; sodium acetate; diisobutylaluminium hydride; copper dichloride; palladium dichloride; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; acetic acid; acetonitrile;

DOI:10.1021/jo972066r

upstream raw materials:

(3-trimethylsilyl-2-propynyl)triphenylphosphonium bromide

[(2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-furan-2-yl]-acetaldehyde

methyl (3R)-4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate

(3aR,5R,6aR)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-furo[3,2-b]furan-2-one

Downstream raw materials:

Acetic acid (2R,3R,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-((E)-5-trimethylsilanyl-pent-2-en-4-ynyl)-tetrahydro-furan-3-yl ester