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

Base Information

• Chemical Name: 2-((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethyl 4-methylbenzenesulfonate
• CAS No.: 287737-64-8
• Molecular Formula: C₃₁H₃₆O₈S
• Molecular Weight: 568.688
• Mol file: 287737-64-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about 2-((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethyl 4-methylbenzenesulfonate 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: 97.0%

p-toluenesulfonyl chloride (98-59-9) + 2-((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethanol (287737-62-6) → 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)

Guidance literature:

With triethylamine; In dichloromethane;

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) → 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)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 91 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

2.1: 80 percent / sodium hydride / dimethylsulfoxide / 1 h / 20 °C

3.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 20 °C

3.2: 93 percent / hydrogen peroxide; NaOH / tetrahydrofuran; H₂O / 30 h / 30 - 50 °C

4.1: 94 percent / triethylamine; N,N-dimethylaminopyridine / CH₂Cl₂ / 20 °C

With dmap; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; 1.1: Swern oxidation / 2.1: Wittig reaction;

DOI:10.1016/S0968-0896(03)00115-9

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) → 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)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 80 percent / sodium hydride / dimethylsulfoxide / 1 h / 20 °C

2.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 20 °C

2.2: 93 percent / hydrogen peroxide; NaOH / tetrahydrofuran; H₂O / 30 h / 30 - 50 °C

3.1: 94 percent / triethylamine; N,N-dimethylaminopyridine / CH₂Cl₂ / 20 °C

With dmap; sodium hydride; triethylamine; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; 1.1: Wittig reaction;

DOI:10.1016/S0968-0896(03)00115-9

upstream raw materials:

p-toluenesulfonyl chloride

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

((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:

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

3,5-di-O-benzyl-4-C-(p-toluenesulfonyloxyethyl)-1,2-di-O-acetyl-β-D-erythropentofuranose

3',5'-di-O-benzyl-2'-O,4'-C-ethylene-5-methyluridine

5'-O-(4,4'-dimethoxytrityl)-2'-O,4'-C-ethylene-5-methyluridine