2,3-O-isopropylidene-5-O-methylsulfonyl-D-ribofuranose

Base Information

• Chemical Name: 2,3-O-isopropylidene-5-O-methylsulfonyl-D-ribofuranose
• CAS No.: 20689-05-8
• Molecular Formula: C₉H₁₆O₇S
• Molecular Weight: 268.288
• Mol file: 20689-05-8.mol

Synonyms:

Chemical Property of 2,3-O-isopropylidene-5-O-methylsulfonyl-D-ribofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3-O-isopropylidene-5-O-methylsulfonyl-D-ribofuranose

There total 1 articles about 2,3-O-isopropylidene-5-O-methylsulfonyl-D-ribofuranose 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:

benzoyl 2,3-O-isopropylidene-5-O-methylsulfonyl-α-D-lyxofuranoside (129033-99-4) + thiophenol (108-98-5) → 5-deoxy-2,3-O-isopropylidene-5-phenylthio-α-D-lyxofuranose (129034-00-0) + 2,3-O-isopropylidene-5-O-methylsulfonyl-α-D-lyxofuranose (20689-05-8)

Guidance literature:

With sodium methylate; Yield given. Multistep reaction. Yields of byproduct given; 1) methanol;

Reference yield:

2,3-O-isopropylidene-5-O-methylsulfonyl-D-ribofuranose (20689-05-8,22169-53-5,141781-86-4,141781-87-5) → (-)-(2R,3R,4S,5R)-N-(benzyloxycarbonyl)-5-O-(t-butyldimethylsilyl)-3,4-O-isopropylidene-2,3,4,5-piperidinetetrol (127181-10-6)

Guidance literature:

Multi-step reaction with 7 steps

1: NaN₃ / dimethylsulfoxide / 2 h / 65 °C

2: pyridine, CrO₃ / CH₂Cl₂ / 0.5 h / Ambient temperature

3: H₂ / Raney Ni / methanol / 2 h / Ambient temperature

4: 93 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

5: 96 percent / NaH / dimethylformamide / 2 h / Ambient temperature

6: 92 percent / sodium borohydride / ethanol / Ambient temperature

7: 1) dimethyl sulfoxide, oxalyl dichloride; 3) triethylamine / 1) CH₂Cl₂, -60 deg C, 5 min; 2) CH₂Cl₂, -60 deg C, 15 min; 3) CH₂Cl₂, -60 deg C, 10 min, then room temp.

With pyridine; 1H-imidazole; chromium(VI) oxide; sodium tetrahydroborate; sodium azide; oxalyl dichloride; hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine; nickel; In methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.65.978

Reference yield:

2,3-O-isopropylidene-5-O-methylsulfonyl-D-ribofuranose (20689-05-8,22169-53-5,141781-86-4,141781-87-5) → (+)-(4R,5S,6R)-6-acetamido-N-(benzyloxycarbonyl)-2,3-didehydro-4,5-(isopropylidenedioxy)-3-piperidinecarboxylic acid (141781-99-9)

Guidance literature:

Multi-step reaction with 15 steps

1: NaN₃ / dimethylsulfoxide / 2 h / 65 °C

2: pyridine, CrO₃ / CH₂Cl₂ / 0.5 h / Ambient temperature

3: H₂ / Raney Ni / methanol / 2 h / Ambient temperature

4: 93 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

5: 96 percent / NaH / dimethylformamide / 2 h / Ambient temperature

6: 92 percent / sodium borohydride / ethanol / Ambient temperature

7: 1) dimethyl sulfoxide, oxalyl dichloride; 3) triethylamine / 1) CH₂Cl₂, -60 deg C, 5 min; 2) CH₂Cl₂, -60 deg C, 15 min; 3) CH₂Cl₂, -60 deg C, 10 min, then room temp.

8: 98 percent / triphenylphosphine, diethyl azodicarboxylate / dimethylformamide / Ambient temperature

9: 1.) hydrazine, 2.) pyridine / 1.) methanol, 30 deg C, 1 d, 2.) RT, overnight

10: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

11: 98 percent / RuO₄ / CCl₄; CH₂Cl₂ / 1 h / Ambient temperature

12: 100 percent / NaH / 1,2-dimethoxy-ethane / 2 h / Ambient temperature

13: 1.) acetic anhydride, p-toluenesulfonic acid, 2.) K₂CO₃ / 1.) RT, overnight, 2.) benzene, RT, overnight

14: pyridine / 168 h / 38 °C

15: aq. NaClO₂, aq. NaH₂PO₄ / 2-methyl-propan-2-ol; various solvent(s) / 24 h / Ambient temperature

With pyridine; 1H-imidazole; chromium(VI) oxide; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; sodium azide; ruthenium tetroxide; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; acetic anhydride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; hydrazine; diethylazodicarboxylate; nickel; In tetrahydrofuran; methanol; tetrachloromethane; 1,2-dimethoxyethane; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1246/bcsj.65.978

upstream raw materials:

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

thiophenol

Downstream raw materials:

(+)-(2R,3S,4R,5R)-2-acetamido-N-(benzyloxycarbonyl)-3,4-O-isopropylidene-3,4,5-piperidinetriol

(-)-(2R,3S,4R,5S)-2-acetamido-N-(benzyloxycarbonyl)-5-(hydroxymethyl)-3,4-O-isopropylidene-3,4-piperidinediol

(+)-(4S,5S,6R)-6-acetamido-N-(benzyloxycarbonyl)-4,5-(isopropylidenedioxy)-3-piperidinone

(-)-(2S,3S,4R)-5-benzyloxycarbonylamino-4-(t-butyldimethylsilyloxy)-2,3-(isopropylidenedioxy)-1-pentanol