(-)-(2R,3R,4S,5R)-N-(benzyloxycarbonyl)-5-O-(t-butyldimethylsilyl)-3,4-O-isopropylidene-2,3,4,5-piperidinetetrol

Base Information

• Chemical Name: (-)-(2R,3R,4S,5R)-N-(benzyloxycarbonyl)-5-O-(t-butyldimethylsilyl)-3,4-O-isopropylidene-2,3,4,5-piperidinetetrol
• CAS No.: 127181-10-6
• Molecular Formula: C₂₂H₃₅NO₆Si
• Molecular Weight: 437.608
• Mol file: 127181-10-6.mol

Synonyms:(-)-(2R,3R,4S,5R)-N-(benzyloxycarbonyl)-5-O-(t-butyldimethylsilyl)-3,4-O-isopropylidene-2,3,4,5-piperidinetetrol

Chemical Property of (-)-(2R,3R,4S,5R)-N-(benzyloxycarbonyl)-5-O-(t-butyldimethylsilyl)-3,4-O-isopropylidene-2,3,4,5-piperidinetetrol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(2R,3R,4S,5R)-N-(benzyloxycarbonyl)-5-O-(t-butyldimethylsilyl)-3,4-O-isopropylidene-2,3,4,5-piperidinetetrol

There total 9 articles about (-)-(2R,3R,4S,5R)-N-(benzyloxycarbonyl)-5-O-(t-butyldimethylsilyl)-3,4-O-isopropylidene-2,3,4,5-piperidinetetrol 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: 88.0%

5-N-(benzyloxycarbonyl)-4-O-(t-butyldimethylsilyl)-5-deoxy-2,3-O-isopropylidene-D-1,5-ribonolactam (117097-25-3,141781-90-0,141781-94-4) → (-)-(2R,3R,4S,5R)-N-(benzyloxycarbonyl)-5-O-(t-butyldimethylsilyl)-3,4-O-isopropylidene-2,3,4,5-piperidinetetrol (127181-10-6)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1246/bcsj.65.978

Reference yield:

2,3-O-isopropylidene-D-ribofuranose (67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1) → (-)-(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 8 steps

1: pyridine / -30 °C

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

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

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

5: 93 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

6: 96 percent / NaH / dimethylformamide / 2 h / Ambient temperature

7: 92 percent / sodium borohydride / ethanol / Ambient temperature

8: 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:

D-Ribose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) → (-)-(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 9 steps

1: p-toluenesulfonic acid monohydrate / a) 10 deg C, 1h, b) RT, 3 h

2: pyridine / -30 °C

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

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

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

6: 93 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

7: 96 percent / NaH / dimethylformamide / 2 h / Ambient temperature

8: 92 percent / sodium borohydride / ethanol / Ambient temperature

9: 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; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; nickel; In methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.65.978

upstream raw materials:

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

5-N-(benzyloxycarbonyl)-4-O-(t-butyldimethylsilyl)-5-deoxy-2,3-O-isopropylidene-D-1,5-ribonolactam

2,3-O-isopropylidene-D-ribofuranose

D-Ribose

Downstream raw materials:

(-)-(2R,3S,4S,5R)-N-(benzyloxycarbonyl)-5-O-(t-butyldimethylsilyl)-3,4-O-isopropylidene-2-phthalimido-3,4,5-piperidinetriol

(+)-(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