3-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-C-(thiazol-2-yl)-β-L-lyxofuranose

Base Information

• Chemical Name: 3-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-C-(thiazol-2-yl)-β-L-lyxofuranose
• CAS No.: 866429-28-9
• Molecular Formula: C₁₈H₂₁NO₄S
• Molecular Weight: 347.435
• Mol file: 866429-28-9.mol

Synonyms:3-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-C-(thiazol-2-yl)-β-L-lyxofuranose

Chemical Property of 3-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-C-(thiazol-2-yl)-β-L-lyxofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-C-(thiazol-2-yl)-β-L-lyxofuranose

There total 2 articles about 3-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-C-(thiazol-2-yl)-β-L-lyxofuranose 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: 95.0%

5-deoxy-1,2-O-isopropylidene-3-C-(thiazol-2-yl)-β-L-lyxofuranose (866429-27-8) + benzyl bromide (100-39-0) → 3-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-C-(thiazol-2-yl)-β-L-lyxofuranose (866429-28-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1021/jo051012b

Reference yield:

1,2-O-Isopropyliden-5-desoxy-β-L-threo-pentofuranos-3-ulose (37111-48-1) → 3-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-C-(thiazol-2-yl)-β-L-lyxofuranose (866429-28-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: BuLi / CH₂Cl₂; hexane / 0.5 h / -78 °C

1.2: 70 percent / CH₂Cl₂; hexane / 1 h / -78 °C

2.1: 95 percent / sodium hydride / dimethylformamide; various solvent(s) / 4 h / 20 °C

With n-butyllithium; sodium hydride; In hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo051012b

Reference yield:

3-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-C-(thiazol-2-yl)-β-L-lyxofuranose (866429-28-9) → 3-O-benzyl-5-deoxy-3-C-formyl-1,2-O-isopropylidene-β-L-lyxofuranose (866429-29-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetonitrile / 0.5 h / 20 °C

2.1: NaBH₄ / methanol / 0.17 h

2.2: 0.113 g / silver nitrate / H₂O; acetonitrile / 0.17 h

With sodium tetrahydroborate; In methanol; acetonitrile;

DOI:10.1021/jo051012b

upstream raw materials:

5-deoxy-1,2-O-isopropylidene-3-C-(thiazol-2-yl)-β-L-lyxofuranose

benzyl bromide

1,2-O-Isopropyliden-5-desoxy-β-L-threo-pentofuranos-3-ulose

Downstream raw materials:

3-O-benzyl-5-deoxy-3-C-formyl-1,2-O-isopropylidene-β-L-lyxofuranose

3-O-benzyl-3-C-carboxy-5-deoxy-1,2-O-isopropylidene-β-L-lyxofuranose