[2',2'-dimethoxyethyl]-2-O-[2'-benzyloxyethyl]-6-O-isobutyl-3,4-di-O-methyl-β-D-mannopyranoside

Base Information

• Chemical Name: [2',2'-dimethoxyethyl]-2-O-[2'-benzyloxyethyl]-6-O-isobutyl-3,4-di-O-methyl-β-D-mannopyranoside
• CAS No.: 400835-52-1
• Molecular Formula: C₂₅H₄₂O₉
• Molecular Weight: 486.603
• Mol file: 400835-52-1.mol

Synonyms:[2',2'-dimethoxyethyl]-2-O-[2'-benzyloxyethyl]-6-O-isobutyl-3,4-di-O-methyl-β-D-mannopyranoside

Chemical Property of [2',2'-dimethoxyethyl]-2-O-[2'-benzyloxyethyl]-6-O-isobutyl-3,4-di-O-methyl-β-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [2',2'-dimethoxyethyl]-2-O-[2'-benzyloxyethyl]-6-O-isobutyl-3,4-di-O-methyl-β-D-mannopyranoside

There total 8 articles about [2',2'-dimethoxyethyl]-2-O-[2'-benzyloxyethyl]-6-O-isobutyl-3,4-di-O-methyl-β-D-mannopyranoside 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:

ethyl-2-O-benzyl-6-O-isobutyl-3,4-di-O-methyl-1-thio-α-D-mannopyranoside (400835-49-6) → [2',2'-dimethoxyethyl]-2-O-[2'-benzyloxyethyl]-6-O-isobutyl-3,4-di-O-methyl-β-D-mannopyranoside (400835-52-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / N-iodosuccinimide; AgOTf; 4A mol. sieves / CH₂Cl₂; toluene / 0 °C

2: 98 percent / H₂ / Pd/C / methanol; H₂O / 1 h / 20 °C

3: KOH / dimethylsulfoxide

With potassium hydroxide; N-iodo-succinimide; 4 A molecular sieve; hydrogen; silver trifluoromethanesulfonate; palladium on activated charcoal; In methanol; dichloromethane; water; dimethyl sulfoxide; toluene; 3: Williamson reaction;

DOI:10.1021/jm020487h

Reference yield:

(3S,4S,5R,6R)-3-Benzyloxy-2-chloro-6-isobutoxymethyl-4,5-dimethoxy-tetrahydro-pyran → [2',2'-dimethoxyethyl]-2-O-[2'-benzyloxyethyl]-6-O-isobutyl-3,4-di-O-methyl-β-D-mannopyranoside (400835-52-1)

Guidance literature:

Multi-step reaction with 3 steps

1: Ag₂CO₃ / CH₂Cl₂ / 20 °C

2: H₂ / Pd/C

3: KN(SiMe₃)2 / tetrahydrofuran

With hydrogen; potassium hexamethylsilazane; silver carbonate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane;

DOI:10.1002/1521-3773(20011015)40:20<3870::AID-ANIE3870>3.0.CO;2-X

Reference yield:

(3S,4S,5R,6R)-3-Benzyloxy-6-isobutoxymethyl-4,5-dimethoxy-tetrahydro-pyran-2-ol → [2',2'-dimethoxyethyl]-2-O-[2'-benzyloxyethyl]-6-O-isobutyl-3,4-di-O-methyl-β-D-mannopyranoside (400835-52-1)

Guidance literature:

Multi-step reaction with 4 steps

1: SOCl₂ / CH₂Cl₂

2: Ag₂CO₃ / CH₂Cl₂ / 20 °C

3: H₂ / Pd/C

4: KN(SiMe₃)2 / tetrahydrofuran

With thionyl chloride; hydrogen; potassium hexamethylsilazane; silver carbonate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane;

DOI:10.1002/1521-3773(20011015)40:20<3870::AID-ANIE3870>3.0.CO;2-X

upstream raw materials:

bromoethyl-2-benzyl ether

(2R,3S,4R,5R,6R)-2-(2,2-Dimethoxy-ethoxy)-6-isobutoxymethyl-4,5-dimethoxy-tetrahydro-pyran-3-ol

ethyl-2-O-benzyl-6-O-isobutyl-3,4-di-O-methyl-1-thio-α-D-mannopyranoside

(2R,3S,4S,5R,6R)-3-Benzyloxy-2-(2,2-dimethoxy-ethoxy)-6-isobutoxymethyl-4,5-dimethoxy-tetrahydro-pyran