1,5-Anhydro-4-O-<3,4-bis-O-(tert-butyldiphenylsilyl)-6-deoxy-2-phenylseleno-β-L-gluco-pyranosyl>-3-O-(tert-butyldimethylsilyl)-2,6-dideoxy-L-arabino-hex-1-enitol

Base Information

• Chemical Name: 1,5-Anhydro-4-O-<3,4-bis-O-(tert-butyldiphenylsilyl)-6-deoxy-2-phenylseleno-β-L-gluco-pyranosyl>-3-O-(tert-butyldimethylsilyl)-2,6-dideoxy-L-arabino-hex-1-enitol
• CAS No.: 221657-61-0
• Molecular Formula: C₅₆H₇₄O₆SeSi₃
• Molecular Weight: 1006.42
• Mol file: 221657-61-0.mol

Synonyms:1,5-Anhydro-4-O-<3,4-bis-O-(tert-butyldiphenylsilyl)-6-deoxy-2-phenylseleno-β-L-gluco-pyranosyl>-3-O-(tert-butyldimethylsilyl)-2,6-dideoxy-L-arabino-hex-1-enitol

Chemical Property of 1,5-Anhydro-4-O-<3,4-bis-O-(tert-butyldiphenylsilyl)-6-deoxy-2-phenylseleno-β-L-gluco-pyranosyl>-3-O-(tert-butyldimethylsilyl)-2,6-dideoxy-L-arabino-hex-1-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,5-Anhydro-4-O-<3,4-bis-O-(tert-butyldiphenylsilyl)-6-deoxy-2-phenylseleno-β-L-gluco-pyranosyl>-3-O-(tert-butyldimethylsilyl)-2,6-dideoxy-L-arabino-hex-1-enitol

There total 3 articles about 1,5-Anhydro-4-O-<3,4-bis-O-(tert-butyldiphenylsilyl)-6-deoxy-2-phenylseleno-β-L-gluco-pyranosyl>-3-O-(tert-butyldimethylsilyl)-2,6-dideoxy-L-arabino-hex-1-enitol 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: 59.0%

(2S,3S,4S)-4-(tert-butyldimethylsilyloxy)-3,4-dihydro-3-hydroxy-2-methyl-2H-pyran (101856-96-6) + Acetyl 3,4-bis-O-(tert-butyldiphenylsilyl)-6-deoxy-2-phenylseleno-β-L-gluco-pyranose (221657-96-1) → 1,5-Anhydro-4-O-<3,4-bis-O-(tert-butyldiphenylsilyl)-6-deoxy-2-phenylseleno-β-L-gluco-pyranosyl>-3-O-(tert-butyldimethylsilyl)-2,6-dideoxy-L-arabino-hex-1-enitol (221657-61-0)

Guidance literature:

With triisopropylsilyl trifluoromethanesulfonate; In diethyl ether; 1.) -80 deg C, 10 min, 2.) -50 deg C, 10 min;

DOI:10.1039/a807479h

Reference yield:

Phenylselenyl chloride (5707-04-0) → 1,5-Anhydro-4-O-<3,4-bis-O-(tert-butyldiphenylsilyl)-6-deoxy-2-phenylseleno-β-L-gluco-pyranosyl>-3-O-(tert-butyldimethylsilyl)-2,6-dideoxy-L-arabino-hex-1-enitol (221657-61-0)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 3 h / Ambient temperature

2: 59 percent / TIPSOTf / diethyl ether / 1.) -80 deg C, 10 min, 2.) -50 deg C, 10 min

With triisopropylsilyl trifluoromethanesulfonate; In diethyl ether; toluene;

DOI:10.1039/a807479h

Reference yield:

3,4-di-O-tertiary-butyldiphenylsilyl-L-rhamnal → 1,5-Anhydro-4-O-<3,4-bis-O-(tert-butyldiphenylsilyl)-6-deoxy-2-phenylseleno-β-L-gluco-pyranosyl>-3-O-(tert-butyldimethylsilyl)-2,6-dideoxy-L-arabino-hex-1-enitol (221657-61-0)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 3 h / Ambient temperature

2: 59 percent / TIPSOTf / diethyl ether / 1.) -80 deg C, 10 min, 2.) -50 deg C, 10 min

With triisopropylsilyl trifluoromethanesulfonate; In diethyl ether; toluene;

DOI:10.1039/a807479h

upstream raw materials:

(2S,3S,4S)-4-(tert-butyldimethylsilyloxy)-3,4-dihydro-3-hydroxy-2-methyl-2H-pyran

Acetyl 3,4-bis-O-(tert-butyldiphenylsilyl)-6-deoxy-2-phenylseleno-β-L-gluco-pyranose

Phenylselenyl chloride

Downstream raw materials:

1,5-Anhydro-4-O-<3,4-bis-O-(tert-butyldiphenylsilyl)-6-deoxy-2-phenylseleno-β-L-gluco-pyranosyl>-2,6-dideoxy-L-erythro-hex-1-en-3-ulose