(4R,5R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-yl acetate

Base Information

• Chemical Name: (4R,5R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-yl acetate
• CAS No.: 529495-78-1
• Molecular Formula: C₂₇H₃₈O₄S₃Si
• Molecular Weight: 550.88
• Mol file: 529495-78-1.mol

Synonyms:(4R,5R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-yl acetate

Chemical Property of (4R,5R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-yl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-yl acetate

There total 3 articles about (4R,5R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-yl acetate 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: 65.0%

acetyl chloride (75-36-5) + (4R,5R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-ol → (4R,5R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-yl acetate (529495-78-1)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1016/S0968-0896(02)00460-1

Reference yield:

(R)-(+)-5-(tert-butyldiphenylsilanyloxymethyl)furan-2(5H)-one (110171-24-9) → (4R,5R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-yl acetate (529495-78-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

2: DIBAL / toluene; hexane / 1 h / -70 °C

3: 65 percent / pyridine / CH₂Cl₂ / 1.5 h / 20 °C

With pyridine; n-butyllithium; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; toluene;

DOI:10.1016/S0968-0896(02)00460-1

Reference yield:

(4R,5R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-one (529495-75-8) → (4R,5R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-yl acetate (529495-78-1)

Guidance literature:

Multi-step reaction with 2 steps

1: DIBAL / toluene; hexane / 1 h / -70 °C

2: 65 percent / pyridine / CH₂Cl₂ / 1.5 h / 20 °C

With pyridine; diisobutylaluminium hydride; In hexane; dichloromethane; toluene;

DOI:10.1016/S0968-0896(02)00460-1

upstream raw materials:

acetyl chloride

(R)-(+)-5-(tert-butyldiphenylsilanyloxymethyl)furan-2(5H)-one

(4R,5R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-one

Downstream raw materials:

1-[5'-O-tert-butyldiphenylsilyl-2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]uracil

N-benzoyl-1-[2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine-5'-(2-cyanoethyl hexadecyl phosphate)

N-benzoyl-1-[5'-O-tert-butyldiphenylsilyl-2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine

N-benzoyl-1-[2',3'-dideoxy-3'-C-tris(methylthio)methyl-β-L-erythro-pentofuranosyl]cytosine