6,8-di-O-acetyl-3,7-anhydro-2,4,5-trideoxy-1-phenyloct-4-enose

Base Information

• Chemical Name: 6,8-di-O-acetyl-3,7-anhydro-2,4,5-trideoxy-1-phenyloct-4-enose
• CAS No.: 81668-62-4
• Molecular Formula: C18H20 O6
• Molecular Weight: 332.353
• Mol file: 81668-62-4.mol

Synonyms:NSC 355509

Chemical Property of 6,8-di-O-acetyl-3,7-anhydro-2,4,5-trideoxy-1-phenyloct-4-enose

Chemical Property:

• Vapor Pressure: 2.51E-08mmHg at 25°C
• Boiling Point: 451°C at 760 mmHg
• Flash Point: 197.7°C
• Density: 1.22g/cm³

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6,8-di-O-acetyl-3,7-anhydro-2,4,5-trideoxy-1-phenyloct-4-enose

There total 11 articles about 6,8-di-O-acetyl-3,7-anhydro-2,4,5-trideoxy-1-phenyloct-4-enose 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: 79.0%

1-styrenyloxytrimethylsilane (13735-81-4) + D-glucal triacetate (2873-29-2) → α-(4',6'-Di-O-acetyl-2',3'-dideoxy-β-D-erythro-hex-2'-enopyranosyl)acetophenone (81668-62-4) + α-(4',6'-Di-O-acetyl-2',3'-dideoxy-α-D-erythro-hex-2'-enopyranosyl)acetophenone (81668-63-5)

Guidance literature:

boron trifluoride diethyl etherate; In dichloromethane; 1.) -45 deg C, 2.) 0 deg C;

DOI:10.1021/jo00177a027

Reference yield: 65.0%

acetophenone (98-86-2) + D-glucal triacetate (2873-29-2) → α-(4',6'-Di-O-acetyl-2',3'-dideoxy-β-D-erythro-hex-2'-enopyranosyl)acetophenone (81668-62-4)

Guidance literature:

acetophenone; With t-butyldimethylsiyl triflate; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 0.333333h; Inert atmosphere;

D-glucal triacetate; In dichloromethane; at 0 - 30 ℃; Reagent/catalyst; Solvent; Inert atmosphere;

DOI:10.1016/j.carres.2016.11.018

Reference yield: 31.0%

1-styrenyloxytrimethylsilane (13735-81-4) + ethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside (3323-72-6) → Acetic acid (Z)-(S)-1-((R)-2-acetoxy-1-hydroxy-ethyl)-4-ethoxy-6-oxo-6-phenyl-hex-2-enyl ester (81668-66-8) + α-(4',6'-Di-O-acetyl-2',3'-dideoxy-β-D-erythro-hex-2'-enopyranosyl)acetophenone (81668-62-4) + α-(4',6'-Di-O-acetyl-2',3'-dideoxy-α-D-erythro-hex-2'-enopyranosyl)acetophenone (81668-63-5)

Guidance literature:

aluminium trichloride; In dichloromethane; for 0.75h; Yields of byproduct given; 1.) -45 deg C, 2.) 0 deg C;

DOI:10.1021/jo00177a027

upstream raw materials:

1-styrenyloxytrimethylsilane

Triacetyl-D-pseudoglucal

isopropyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

1,4,6-Tri-O-acetyl-α,β-D-erythro-hex-2-enopyranose (Pseudo-C-glucal triacetate)

Downstream raw materials:

α-(4',6'-Di-O-acetyl-2',3'-dideoxy-α-D-erythro-hex-2'-enopyranosyl)acetophenone

Acetic acid (2S,6R)-6-(2-oxo-2-phenyl-ethyl)-3,6-dihydro-2H-pyran-2-ylmethyl ester

Acetic acid (2S,6S)-6-(2-oxo-2-phenyl-ethyl)-5,6-dihydro-2H-pyran-2-ylmethyl ester

Refernces

• 1、 Takhi, Mohamed,Abdel Rahman, Adel A.-H.,Schmidt, Richard R.. "Yb(OTf)3-catalyzed C-glycosylation: Highly stereoselective synthesis of C-pseudoglycals". . p. 4053 - 4056. Retrieved 2001.
• 2、 Malkov, Andrei V.,Farn, Benjamin P.,Hussain, Nigel,Kocovsky, Pavel. "Molybdenum-catalyzed allylic substitution in glycals: A C-C bond-forming Ferrier-type reaction". . p. 1735 - 1745. Retrieved 2007/10/03.