2,3,5-tri-O-benzyl-4-O-tert-butyldimethylsilyl-L-arabinose ethylenedithioacetal

Base Information

• Chemical Name: 2,3,5-tri-O-benzyl-4-O-tert-butyldimethylsilyl-L-arabinose ethylenedithioacetal
• CAS No.: 613234-28-9
• Molecular Formula: C₃₄H₄₆O₄S₂Si
• Molecular Weight: 610.954
• Mol file: 613234-28-9.mol

Synonyms:2,3,5-tri-O-benzyl-4-O-tert-butyldimethylsilyl-L-arabinose ethylenedithioacetal

Chemical Property of 2,3,5-tri-O-benzyl-4-O-tert-butyldimethylsilyl-L-arabinose ethylenedithioacetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,5-tri-O-benzyl-4-O-tert-butyldimethylsilyl-L-arabinose ethylenedithioacetal

There total 1 articles about 2,3,5-tri-O-benzyl-4-O-tert-butyldimethylsilyl-L-arabinose ethylenedithioacetal 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: 82.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 2,3,5-tri-O-benzyl-L-arabinose ethylenedithioacetal (613234-27-8) → 2,3,5-tri-O-benzyl-4-O-tert-butyldimethylsilyl-L-arabinose ethylenedithioacetal (613234-28-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 80 ℃; for 20h;

DOI:10.1016/S0040-4020(03)01055-X

Reference yield: 48.6%

2,3,5-tri-O-benzyl-4-O-tert-butyldimethylsilyl-L-arabinose ethylenedithioacetal (613234-28-9) → 2,3,5-tri-O-benzyl-4-O-tert-butyldimethylsilyl-L-arabinose (613234-29-0)

Guidance literature:

With sodium carbonate; methyl iodide; In water; acetone; for 16h; Heating;

DOI:10.1016/S0040-4020(03)01055-X

Reference yield:

2,3,5-tri-O-benzyl-4-O-tert-butyldimethylsilyl-L-arabinose ethylenedithioacetal (613234-28-9) → (5R,6S,7R,8R)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyridine (613234-34-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 48.6 percent / Na₂CO₃; MeI / acetone; H₂O / 16 h / Heating

2.1: n-BuLi; tert-butyldimethylsilyl chloride / hexane; tetrahydrofuran / 0.33 h / -50 °C

2.2: 31 percent / tetrahydrofuran; hexane / 3 h / -70 - 20 °C

3.1: NaH / dimethylformamide; various solvent(s) / 0 - 20 °C

4.1: 300 mg / hydrochloric acid / tetrahydrofuran; H₂O / 2 h / Heating

5.1: pyridine / 1 h / 0 - 20 °C

6.1: 39 mg / acetic anhydride / 20 h / 80 °C

With pyridine; hydrogenchloride; n-butyllithium; acetic anhydride; sodium hydride; sodium carbonate; tert-butyldimethylsilyl chloride; methyl iodide; In tetrahydrofuran; hexane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4020(03)01055-X

upstream raw materials:

tert-butyldimethylsilyl chloride

2,3,5-tri-O-benzyl-L-arabinose ethylenedithioacetal

Downstream raw materials:

2,3,5-tri-O-benzyl-4-O-tert-butyldimethylsilyl-L-arabinose

(5R,6S,7R,8S)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyridine

(5R,6S,7R,8R)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyridine

2-(tert-butyl-dimethyl-silanyl)-5-[2,3,5-tris-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-pentyl]-imidazole-1-sulfonic acid dimethylamide