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

Base Information

• Chemical Name: (1R,2R)-3-O-benzyl-1,2-O-isopropylidene-1-(2-thiazolyl)-1,2,3-propanetriol
• CAS No.: 141873-77-0
• Molecular Formula: C₁₆H₁₉NO₃S
• Molecular Weight: 305.398
• Mol file: 141873-77-0.mol

Synonyms:

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

There total 5 articles about (1R,2R)-3-O-benzyl-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:

(2R,3R)-1,2-O-Isopropylidene-3-(2-thiazolyl)-1,2,3-propanetriol (103795-10-4) → (1R,2R)-3-O-benzyl-1,2-O-isopropylidene-1-(2-thiazolyl)-1,2,3-propanetriol (141873-77-0)

Guidance literature:

Multi-step reaction with 5 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

4: 100 percent / Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

5: 1.) 60percent NaH / 1.) DMF, -15 deg C, 10 min., 2.) r.t., 2 h

With dmap; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; In tetrahydrofuran; 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-benzyl-1,2-O-isopropylidene-1-(2-thiazolyl)-1,2,3-propanetriol (141873-77-0)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: 100 percent / Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

4: 1.) 60percent NaH / 1.) DMF, -15 deg C, 10 min., 2.) r.t., 2 h

With dmap; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; benzene;

DOI:10.1055/s-1992-34166

Reference yield:

(1R,2R)-3-O-(tert-butyldiphenylsilyl)-1-(2-thiazolyl)-1,2,3-propanetriol (141873-72-5) → (1R,2R)-3-O-benzyl-1,2-O-isopropylidene-1-(2-thiazolyl)-1,2,3-propanetriol (141873-77-0)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 100 percent / Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

3: 1.) 60percent NaH / 1.) DMF, -15 deg C, 10 min., 2.) r.t., 2 h

With tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; benzene;

DOI:10.1055/s-1992-34166

upstream raw materials:

benzyl bromide

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

(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:

4-O-benzyl-2,3-O-isopropylidene-D-threose

(4R,5S)-4,5-bis((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolane

methyl 6-O-benzyl-3-benzylamino-2,3-dideoxy-α-D-arabinopyranoside

(3R,4R,5R)-3-benzyl(tert-butoxycarbonyl)amino-6-benzyloxy-4,5-isopropylidenedioxyhexanal