(-)-(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
Hs Code.:

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

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

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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%

: 117097-25-3,141781-90-0,141781-94-4
5-N-(benzyloxycarbonyl)-4-O-(t-butyldimethylsilyl)-5-deoxy-2,3-O-isopropylidene-D-1,5-ribonolactam

: 127181-10-6
(-)-(2R,3R,4S,5R)-N-(benzyloxycarbonyl)-5-O-(t-butyldimethylsilyl)-3,4-O-isopropylidene-2,3,4,5-piperidinetetrol

Guidance literature:: With L-Selectride; In tetrahydrofuran; at -78 - 20 ℃;
DOI:10.1246/bcsj.65.978

Reference yield:

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

: 127181-10-6
(-)-(2R,3R,4S,5R)-N-(benzyloxycarbonyl)-5-O-(t-butyldimethylsilyl)-3,4-O-isopropylidene-2,3,4,5-piperidinetetrol

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:

: 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
D-Ribose

: 127181-10-6
(-)-(2R,3R,4S,5R)-N-(benzyloxycarbonyl)-5-O-(t-butyldimethylsilyl)-3,4-O-isopropylidene-2,3,4,5-piperidinetetrol

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