(1R)-1-O-benzyl-2,3-O-isopropylidene-1-(2-thiazolyl)-D-glycitol

Base Information

• Chemical Name: (1R)-1-O-benzyl-2,3-O-isopropylidene-1-(2-thiazolyl)-D-glycitol
• CAS No.: 103795-11-5
• Molecular Formula: C₁₆H₁₉NO₃S
• Molecular Weight: 305.398
• Mol file: 103795-11-5.mol

Synonyms:(1R)-1-O-benzyl-2,3-O-isopropylidene-1-(2-thiazolyl)-D-glycitol

Chemical Property of (1R)-1-O-benzyl-2,3-O-isopropylidene-1-(2-thiazolyl)-D-glycitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R)-1-O-benzyl-2,3-O-isopropylidene-1-(2-thiazolyl)-D-glycitol

There total 3 articles about (1R)-1-O-benzyl-2,3-O-isopropylidene-1-(2-thiazolyl)-D-glycitol 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:

2-[((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-trimethylsilanyloxy-methyl]-thiazole (103795-09-1) → (1R)-1-O-benzyl-2,3-O-isopropylidene-1-(2-thiazolyl)-D-glycitol (103795-11-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1 M tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h

2: 1.) 50percent NaH, 2.) tetra-n-butylammonium iodide / 1.) reflux, 20 min, 2.) room temp., overnight

With tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran;

DOI:10.1021/jo00264a035

Reference yield:

benzyl bromide (100-39-0) + (2R,3R)-1,2-O-Isopropylidene-3-(2-thiazolyl)-1,2,3-propanetriol (103795-10-4) → (1R)-1-O-benzyl-2,3-O-isopropylidene-1-(2-thiazolyl)-D-glycitol (103795-11-5)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; Yield given. Multistep reaction; 1.) reflux, 20 min, 2.) room temp., overnight;

DOI:10.1021/jo00264a035

Reference yield:

2,3-isopropylidene-glyceraldehyde (15186-48-8) → (1R)-1-O-benzyl-2,3-O-isopropylidene-1-(2-thiazolyl)-D-glycitol (103795-11-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) Bu₄NF / 1.) CH₂Cl₂, r. t., 14 h, 2.) THF, 2 h, r. t.

2: 1.) NaH, 2.) Bu₄NI / 1.) THF, reflux, 20 min, 2.) r. t., 14 h

With tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride;

DOI:10.1055/s-1992-34170

upstream raw materials:

benzyl bromide

(2R,3R)-1,2-O-Isopropylidene-3-(2-thiazolyl)-1,2,3-propanetriol

2,3-isopropylidene-glyceraldehyde

2-[((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-trimethylsilanyloxy-methyl]-thiazole

Downstream raw materials:

(R)-2-(benzyloxy)-2-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde

(S)-Benzyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetaldehyde

(2R,3R)-3-Benzyloxy-3-(2-thiazolyl)-1,2,3-propanetriol

2-[(R)-Benzyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-3-methyl-thiazol-3-ium; iodide