Mono-O-benzoyl-1,2;5,6-bis-O-isopropyliden-D-talit

Base Information

• Chemical Name: Mono-O-benzoyl-1,2;5,6-bis-O-isopropyliden-D-talit
• CAS No.: 190008-37-8
• Molecular Formula: C₁₉H₂₆O₇
• Molecular Weight: 366.411
• Mol file: 190008-37-8.mol

Synonyms:Mono-O-benzoyl-1,2;5,6-bis-O-isopropyliden-D-talit

Chemical Property of Mono-O-benzoyl-1,2;5,6-bis-O-isopropyliden-D-talit

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Mono-O-benzoyl-1,2;5,6-bis-O-isopropyliden-D-talit

There total 5 articles about Mono-O-benzoyl-1,2;5,6-bis-O-isopropyliden-D-talit 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:

(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanone (189701-54-0) → Mono-O-benzoyl-1,2;5,6-bis-O-isopropyliden-D-talit (190008-37-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 45 percent / Zn(BH₄)2 / diethyl ether / 5 h / -15 °C

2: 1.) DMAP, 2.) TBAF / 1.) pyridine, 0 deg C, 2.) THF

With dmap; zinc(II) tetrahydroborate; tetrabutyl ammonium fluoride; In diethyl ether;

DOI:10.1021/jo961542v

Reference yield:

(1R,2S)-2-(tert-Butyl-diphenyl-silanyloxy)-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol (189701-50-6) → Mono-O-benzoyl-1,2;5,6-bis-O-isopropyliden-D-talit (190008-37-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / oxalyl chloride, DMSO, TEA / CH₂Cl₂ / 1.) -78 deg C, 15 min, 2.) -78 deg C to 0 deg C

2: 45 percent / Zn(BH₄)2 / diethyl ether / 5 h / -15 °C

3: 1.) DMAP, 2.) TBAF / 1.) pyridine, 0 deg C, 2.) THF

With dmap; zinc(II) tetrahydroborate; oxalyl dichloride; TEA; tetrabutyl ammonium fluoride; dimethyl sulfoxide; In diethyl ether; dichloromethane;

DOI:10.1021/jo961542v

Reference yield:

1,2:5,6-di-O-isopropylidene-D-mannitol (1707-77-3) → Mono-O-benzoyl-1,2;5,6-bis-O-isopropyliden-D-talit (190008-37-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) LiN(TMS)2 / 1.) THF, hexane, -78 deg C, 30 min, 2.) -78 deg C, 10 min; warm to room temperature

2: 71 percent / Rh₂(pfm)4 / benzene / Heating

With Rh₂(pfm)4; lithium hexamethyldisilazane; In benzene;

DOI:10.1021/jo970625o

upstream raw materials:

benzoyl chloride

(1S,2S)-2-(tert-Butyl-diphenyl-silanyloxy)-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol

(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanone

(1R,2S)-2-(tert-Butyl-diphenyl-silanyloxy)-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol

Downstream raw materials:

Benzoic acid (S)-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-oxo-ethyl ester

Refernces

• 1、 Padwa, Albert,Prein, Michael. "π-Facial Diastereoselection in [3 + 2]-Cycloadditions of Isomuenchnone Dipoles". . p. 6842 - 6854. Retrieved 2007/10/03.