(3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-5-(2-(tosyloxy)ethyl)tetrahydrofuran-2,3-diyl diacetate

Base Information

• Chemical Name: (3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-5-(2-(tosyloxy)ethyl)tetrahydrofuran-2,3-diyl diacetate
• CAS No.: 452949-21-2
• Molecular Formula: C₃₂H₃₆O₁₀S
• Molecular Weight: 612.698
• Mol file: 452949-21-2.mol

Synonyms:(3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-5-(2-(tosyloxy)ethyl)tetrahydrofuran-2,3-diyl diacetate

Chemical Property of (3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-5-(2-(tosyloxy)ethyl)tetrahydrofuran-2,3-diyl diacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-5-(2-(tosyloxy)ethyl)tetrahydrofuran-2,3-diyl diacetate

There total 5 articles about (3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-5-(2-(tosyloxy)ethyl)tetrahydrofuran-2,3-diyl diacetate 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: 86.0%

acetic anhydride (108-24-7) + 2-((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethyl 4-methylbenzenesulfonate (287737-64-8) → (3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-5-(2-(tosyloxy)ethyl)tetrahydrofuran-2,3-diyl diacetate (452949-21-2)

Guidance literature:

With sulfuric acid; In acetic acid;

DOI:10.1016/S0960-894X(01)00683-7

Reference yield:

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol (153186-10-8) → (3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-5-(2-(tosyloxy)ethyl)tetrahydrofuran-2,3-diyl diacetate (452949-21-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 91 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

2.1: 64 percent / NaH / dimethylsulfoxide

3.1: 9-BBN / tetrahydrofuran

3.2: 93 percent / H₂O₂; NaOH / tetrahydrofuran

4.1: 97 percent / Et₃N / CH₂Cl₂

5.1: 86 percent / H₂SO₄ / acetic acid

With 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; sulfuric acid; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; acetic acid; dimethyl sulfoxide; 1.1: Swern oxidation / 2.1: Wittig reaction;

DOI:10.1016/S0960-894X(01)00683-7

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) → (3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-5-(2-(tosyloxy)ethyl)tetrahydrofuran-2,3-diyl diacetate (452949-21-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 64 percent / NaH / dimethylsulfoxide

2.1: 9-BBN / tetrahydrofuran

2.2: 93 percent / H₂O₂; NaOH / tetrahydrofuran

3.1: 97 percent / Et₃N / CH₂Cl₂

4.1: 86 percent / H₂SO₄ / acetic acid

With 9-borabicyclo[3.3.1]nonane dimer; sulfuric acid; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; acetic acid; dimethyl sulfoxide; 1.1: Wittig reaction;

DOI:10.1016/S0960-894X(01)00683-7

upstream raw materials:

acetic anhydride

2-((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethyl 4-methylbenzenesulfonate

((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:

3',5'-di-O-benzyl-4'-C-(p-toluenesulfonyloxyethyl)-2'-O-acetyl-5-methyluridine

3',5'-di-O-benzyl-4'-C-(p-toluenesulfonyloxyethyl)-2'-O-acetyl-uridine

3',5'-di-O-benzyl-4'-C-(p-toluenesulfonyloxyethyl)-2'-O-acetyl-4-N-benzoylcytidine

3',5'-di-O-benzyl-4'-C-(p-toluenesulfonyloxyethyl)-2'-O-acetyl-6-N-benzoyladenosine