Methyl 2,3-dideoxy-α-D-erythro-hexopyranoside diacetate

Base Information

• Chemical Name: Methyl 2,3-dideoxy-α-D-erythro-hexopyranoside diacetate
• CAS No.: 64551-84-4
• Molecular Formula: C11H18O6
• Molecular Weight: 246.26
• Mol file: 64551-84-4.mol

Synonyms:Methyl 2,3-dideoxy-α-D-erythro-hexopyranoside diacetate

Chemical Property of Methyl 2,3-dideoxy-α-D-erythro-hexopyranoside diacetate

Chemical Property:

• PSA: 71.06000
• LogP: 0.63270

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 2,3-dideoxy-α-D-erythro-hexopyranoside diacetate

There total 5 articles about Methyl 2,3-dideoxy-α-D-erythro-hexopyranoside diacetate 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: 65.0%

methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside (3427-20-1,6605-29-4,20701-48-8,62279-49-6,62279-50-9,62279-51-0,87335-80-6,20701-51-3) → methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hexopyranoside (64551-84-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 1h;

DOI:10.1021/ja069342g

Reference yield:

methyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranoside (3427-20-1) → methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hexopyranoside (64551-84-4) + Methyl-4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranosid (93220-64-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;

Reference yield:

D-glucal triacetate (2873-29-2) → methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hexopyranoside (64551-84-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / BF₃*Et₂O / CH₂Cl₂ / 16 h / 20 °C

2: 65 percent / H₂ / Pd/C / ethanol / 1 h / 20 °C

With boron trifluoride diethyl etherate; hydrogen; palladium on activated charcoal; In ethanol; dichloromethane;

DOI:10.1021/ja069342g

upstream raw materials:

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

methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside

D-glucal triacetate

Downstream raw materials:

2-((3S,4R)-3,4-Dimethoxy-5-trityloxy-pentyl)-[1,3]dithiane

(1S,6S,7R)-6,7-Dimethoxy-1-phenyl-8-trityloxy-octan-1-ol

(2R,3S,8S)-8-(tert-butyldimethylsilyloxy)-2,3-dimethoxy-8-phenyloctan-1-ol

(1S,2S,3E,5R,6S,11S,14S,15R,16R,17S,18S)-15,17-dihydroxy-5,6,16-trimethoxy-2,14,18-trimethyl-11-phenyl-12,19-dioxabicyclo[13.3.1]nonadec-3-en-13-one

Refernces

• 1、 Banaag, April R.,Tius, Marcus A.. "Traceless chiral auxiliaries for the allene ether Nazarov cyclization". supporting information; experimental part. p. 8133 - 8141. Retrieved 2009/04/04.
• 2、 Loepfe, Michael,Siegel, Jay S.. "Diastereoselective synthesis of 2′,3′-dideoxy- β-C- glucopyranosides as intermediates for the synthesis of 2′,3′- dideoxy-β-D-glucopyranosyl-C-nucleosides". . p. 1029 - 1035. Retrieved 2008/09/17.