benzoyl 2,3-O-isopropylidene-5-O-methylsulfonyl-α-D-lyxofuranoside

Base Information

• Chemical Name: benzoyl 2,3-O-isopropylidene-5-O-methylsulfonyl-α-D-lyxofuranoside
• CAS No.: 129033-99-4
• Molecular Formula: C₁₆H₂₀O₈S
• Molecular Weight: 372.396
• Mol file: 129033-99-4.mol

Synonyms:

Chemical Property of benzoyl 2,3-O-isopropylidene-5-O-methylsulfonyl-α-D-lyxofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzoyl 2,3-O-isopropylidene-5-O-methylsulfonyl-α-D-lyxofuranoside

There total 2 articles about benzoyl 2,3-O-isopropylidene-5-O-methylsulfonyl-α-D-lyxofuranoside 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:

1-O-benzoyl 2,3-O-isopropylidene-α-D-lyxopentodialdehydo-1,4-furanoside (57492-91-8) → benzoyl 2,3-O-isopropylidene-5-O-methylsulfonyl-α-D-lyxofuranoside (129033-99-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / NaBH₄ / methanol / 0.08 h

2: pyridine / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; sodium tetrahydroborate; In methanol; dichloromethane;

Reference yield:

1-O-benzoyl-2,3-O-isopropylidene-α-D-lyxofuranose (110808-28-1) + methanesulfonyl chloride (124-63-0) → benzoyl 2,3-O-isopropylidene-5-O-methylsulfonyl-α-D-lyxofuranoside (129033-99-4)

Guidance literature:

With pyridine; In dichloromethane; for 2h; Yield given; Ambient temperature;

Reference yield:

benzoyl 2,3-O-isopropylidene-5-O-methylsulfonyl-α-D-lyxofuranoside (129033-99-4) → methyl (methyl 4-O-benzyl-9-O-tert-butyldimethylsilyl-3-deoxy-7,8-O-isopropylidene-D-gluco-2-nonulopyranosid-5-ulos)onate (129063-70-3)

Guidance literature:

Multi-step reaction with 14 steps

1: 1) sodium methoxide / 1) methanol

2: 83 percent / NaBH₄ / methanol / 3 h

3: 92 percent / imidazole / dimethylformamide / 0.75 h / Ambient temperature

4: 98 percent / DMSO, dicyclohexyl carbodiimide, pyridine, trifluoroacetic acid / diethyl ether / 0 deg C then RT, 3 h

5: 82 percent / 3 h / 70 °C

6: 96 percent / aq. sodium hydroxide / ethanol / 3.5 h

7: 99 percent / pyridine / toluene / 1) -10 deg C, 30 min; 2) 0 deg C, 17 h

8: 73 percent / toluene / 72 h / 60 °C / 5250420 Torr

9: 82 percent / potassium carbonate / methanol / 3 h

10: 74 percent / silver oxide / CH₂Cl₂ / 1) RT, 30 min; 2) reflux, 11 h

11: 85 percent / Raney nickel / tetrahydrofuran / 0.33 h / Ambient temperature

12: 1) borane-dimethylsulfide; 2) 10 percent aq. sodium hydroxide, 35 percent H₂O₂ / 1) tetrahydrofuran, -10 deg C then RT, 26 h; 2) -10 deg C, then RT, 20 min

13: 83 percent / imidazole / CH₂Cl₂ / ice bath

14: 95 percent / DCC, DMSO, pyridine, trifluoroacetic acid / diethyl ether / 0 deg C, 15 min then RT, 1 h

With pyridine; 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; dimethylsulfide borane complex; dihydrogen peroxide; sodium methylate; nickel; potassium carbonate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; silver(l) oxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

upstream raw materials:

1-O-benzoyl-2,3-O-isopropylidene-α-D-lyxofuranose

methanesulfonyl chloride

1-O-benzoyl 2,3-O-isopropylidene-α-D-lyxopentodialdehydo-1,4-furanoside

Downstream raw materials:

5-deoxy-2,3-O-isopropylidene-5-phenylthio-α-D-lyxofuranose

2,3-O-isopropylidene-5-O-methylsulfonyl-α-D-lyxofuranose

5-deoxy-2,3-O-isopropylidene-5-phenylthio-D-lyxitol

1-O-tert-butyldimethylsilyl-5-deoxy-2,3-O-isopropylidene-5-phenylthio-D-lyxitol