(((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethynyl)triethylsilane

Base Information

• Chemical Name: (((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethynyl)triethylsilane
• CAS No.: 233266-80-3
• Molecular Formula: C₃₀H₄₀O₅Si
• Molecular Weight: 508.73
• Mol file: 233266-80-3.mol

Synonyms:(((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethynyl)triethylsilane

Chemical Property of (((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethynyl)triethylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethynyl)triethylsilane

There total 8 articles about (((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethynyl)triethylsilane 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: 98.0%

triethylsilyl chloride (994-30-9) + 3,5-di-O-benzyl-4-C-ethynyl-1,2-O-isopropylidene-D-ribo-pentofuranose (233266-78-9) → (((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethynyl)triethylsilane (233266-80-3)

Guidance literature:

With n-butyllithium; In tetrahydrofuran;

DOI:10.1271/bbb.63.1146

Reference yield:

(3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde (233266-76-7) → (((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethynyl)triethylsilane (233266-80-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 95.4 percent / triphenylphosphine / CH₂Cl₂ / 1 h / 0 °C

2.1: 90.2 percent / n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -78 °C

3.2: 97.6 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

With n-butyllithium; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jm000209n

Reference yield:

triethylsilyl chloride (994-30-9) + 3,5-di-O-benzyl-4-C-(2,2-dibromoethenyl)-1,2-O-isopropylidene-α-D-ribo-pentofuranose (233266-77-8) → (((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethynyl)triethylsilane (233266-80-3)

Guidance literature:

3,5-di-O-benzyl-4-C-(2,2-dibromoethenyl)-1,2-O-isopropylidene-α-D-ribo-pentofuranose; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

triethylsilyl chloride; In tetrahydrofuran; hexane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol5036535

upstream raw materials:

triethylsilyl chloride

3,5-di-O-benzyl-4-C-ethynyl-1,2-O-isopropylidene-D-ribo-pentofuranose

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

(3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde

Downstream raw materials:

(2R,3S,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-2-ethynyl-2-(hydroxymethyl)tetrahydrofuran-3-ol monohydrate

(2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((triethylsilyl)ethynyl)tetrahydrofuran-3-yl acetate

1-((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-3-hydroxy-5-((triethylsilyl)ethynyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

(2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((triethylsilyl)ethynyl)tetrahydrofuran-3-yl acetate