((2R,3R)-2,3-bis(benzyloxy)pent-4-enyloxy)(tert-butyl)dimethylsilane

Base Information

• Chemical Name: ((2R,3R)-2,3-bis(benzyloxy)pent-4-enyloxy)(tert-butyl)dimethylsilane
• CAS No.: 535994-48-0
• Molecular Formula: C₂₅H₃₆O₃Si
• Molecular Weight: 412.645
• Mol file: 535994-48-0.mol

Synonyms:((2R,3R)-2,3-bis(benzyloxy)pent-4-enyloxy)(tert-butyl)dimethylsilane

Chemical Property of ((2R,3R)-2,3-bis(benzyloxy)pent-4-enyloxy)(tert-butyl)dimethylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2R,3R)-2,3-bis(benzyloxy)pent-4-enyloxy)(tert-butyl)dimethylsilane

There total 3 articles about ((2R,3R)-2,3-bis(benzyloxy)pent-4-enyloxy)(tert-butyl)dimethylsilane 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: 87.0%

t-butyldimethylsiyl triflate (69739-34-0) + (2R,3R)-2,3-bis(benzyloxy)pent-4-en-1-ol (535994-49-1) → ((2R,3R)-2,3-bis(benzyloxy)pent-4-enyloxy)(tert-butyl)dimethylsilane (535994-48-0)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 1.25h; Inert atmosphere;

DOI:10.1021/ol100123p

Reference yield:

Methyltriphenylphosphonium bromide (1779-49-3) + (2S,3R)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butanal (162630-99-1) → ((2R,3R)-2,3-bis(benzyloxy)pent-4-enyloxy)(tert-butyl)dimethylsilane (535994-48-0)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 23 ℃; for 2h;

DOI:10.1021/ol034347t

Reference yield:

(2R,3R)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butan-1-ol (171622-74-5) → ((2R,3R)-2,3-bis(benzyloxy)pent-4-enyloxy)(tert-butyl)dimethylsilane (535994-48-0)

Guidance literature:

Multi-step reaction with 2 steps

1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 0 - 23 °C

2: 8.15 g / n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 23 °C

With n-butyllithium; Dess-Martin periodane; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/ol034347t

upstream raw materials:

Methyltriphenylphosphonium bromide

(2S,3R)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butanal

(2R,3R)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butan-1-ol

t-butyldimethylsiyl triflate

Downstream raw materials:

(2R,3R)-2,3-bis(benzyloxy)pent-4-en-1-ol

(2S,3R)-2,3-dibenzyloxy-4-penten-1-al