(1R,2R)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-1-(2-thiazolyl)-1,2,3-propanetriol

Base Information

• Chemical Name: (1R,2R)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-1-(2-thiazolyl)-1,2,3-propanetriol
• CAS No.: 141873-73-6
• Molecular Formula: C₂₅H₃₁NO₃SSi
• Molecular Weight: 453.678
• Mol file: 141873-73-6.mol

Synonyms:(1R,2R)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-1-(2-thiazolyl)-1,2,3-propanetriol

Chemical Property of (1R,2R)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-1-(2-thiazolyl)-1,2,3-propanetriol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-1-(2-thiazolyl)-1,2,3-propanetriol

There total 3 articles about (1R,2R)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-1-(2-thiazolyl)-1,2,3-propanetriol 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: 86.0%

(1R,2R)-3-O-(tert-butyldiphenylsilyl)-1-(2-thiazolyl)-1,2,3-propanetriol (141873-72-5) + 2,2-dimethoxy-propane (77-76-9) → (1R,2R)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-1-(2-thiazolyl)-1,2,3-propanetriol (141873-73-6)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 1h; Heating;

DOI:10.1055/s-1992-34166

Reference yield:

(2R,3R)-1,2-O-Isopropylidene-3-(2-thiazolyl)-1,2,3-propanetriol (103795-10-4) → (1R,2R)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-1-(2-thiazolyl)-1,2,3-propanetriol (141873-73-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / 90percent AcOH / H₂O / 0.5 h / 90 °C

2: 96 percent / Et₃N, DMAP / dimethylformamide / 16 h / 25 °C

3: 86 percent / TsOH / benzene / 1 h / Heating

With dmap; toluene-4-sulfonic acid; acetic acid; triethylamine; In water; N,N-dimethyl-formamide; benzene;

DOI:10.1055/s-1992-34166

Reference yield:

(1R,2R)-1-(2-thiazolyl)-1,2,3-propanetriol (141873-71-4) → (1R,2R)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-1-(2-thiazolyl)-1,2,3-propanetriol (141873-73-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / Et₃N, DMAP / dimethylformamide / 16 h / 25 °C

2: 86 percent / TsOH / benzene / 1 h / Heating

With dmap; toluene-4-sulfonic acid; triethylamine; In N,N-dimethyl-formamide; benzene;

DOI:10.1055/s-1992-34166

upstream raw materials:

(1R,2R)-3-O-(tert-butyldiphenylsilyl)-1-(2-thiazolyl)-1,2,3-propanetriol

2,2-dimethoxy-propane

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

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

Downstream raw materials:

(E)-(3S,4R)-5-benzyloxy-3,4-O-isopropylidenedioxy-1-(2-thiazolyl)1-pentene

(Z)-(3S,4R)-5-benzyloxy-3,4-O-isopropylidenedioxy-1-(2-thiazolyl)1-pentene

(S)-((4S,5R)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-thiazol-2-yl-methanol

2-[(E)-2-((4S,5R)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-vinyl]-3-methyl-thiazol-3-ium; iodide