(2S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(3,5-dibenzyl-4-oxo-[1,3,5]triazinan-1-yl)-2-methoxycarbonylmethyl-piperidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(3,5-dibenzyl-4-oxo-[1,3,5]triazinan-1-yl)-2-methoxycarbonylmethyl-piperidine-1-carboxylic acid tert-butyl ester
CAS No.:148064-59-9
Molecular Formula:C₃₆H₅₄N₄O₆Si
Molecular Weight:666.933
Hs Code.:

(2S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(3,5-dibenzyl-4-oxo-[1,3,5]triazinan-1-yl)-2-methoxycarbonylmethyl-piperidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (2S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(3,5-dibenzyl-4-oxo-[1,3,5]triazinan-1-yl)-2-methoxycarbonylmethyl-piperidine-1-carboxylic acid tert-butyl ester

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Technology Process of (2S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(3,5-dibenzyl-4-oxo-[1,3,5]triazinan-1-yl)-2-methoxycarbonylmethyl-piperidine-1-carboxylic acid tert-butyl ester

There total 14 articles about (2S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(3,5-dibenzyl-4-oxo-[1,3,5]triazinan-1-yl)-2-methoxycarbonylmethyl-piperidine-1-carboxylic acid tert-butyl ester 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:

: 1466-67-7
1,3-dibenzylurea

: 148064-59-9
(2S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(3,5-dibenzyl-4-oxo-[1,3,5]triazinan-1-yl)-2-methoxycarbonylmethyl-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 14 steps

1: 2) ethyl acetate, reflux

2: LiBH₄ / diethyl ether

3: Zn(N₃)2(py)2, Ph₃P, DEAD, imid / toluene

4: H₂ / 10percent Pd/C / ethanol

5: pyridine / CH₂Cl₂

6: TBAF / tetrahydrofuran / 0 to 25 deg C

7: (COCl)2, DMSO, DIPEA / CH₂Cl₂

8: BF₃*Et₂O / CH₂Cl₂ / -78 - -20 °C

9: DIPEA / CH₂Cl₂ / 0 °C

10: OsO₄, NMO / acetone; butan-1-ol; H₂O

11: NaIO₄ / tetrahydrofuran; H₂O

12: toluene / 70 °C

13: 85 percent / 8.8 eq. NaBH₄ / methanol

14: DIPEA / CH₂Cl₂

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium borohydride; N-methyl-2-indolinone; oxalyl dichloride; Zn(N₃)2/bis-pyridine complex; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; toluene; butan-1-ol;
DOI:10.1021/jo00062a003

Reference yield:

: 148064-50-0
1,3-Dibenzyl-5-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxymethyl-ethyl]-[1,3,5]triazinan-2-one

: 148064-59-9
(2S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(3,5-dibenzyl-4-oxo-[1,3,5]triazinan-1-yl)-2-methoxycarbonylmethyl-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: Zn(N₃)2(py)2, Ph₃P, DEAD, imid / toluene

2: H₂ / 10percent Pd/C / ethanol

3: pyridine / CH₂Cl₂

4: TBAF / tetrahydrofuran / 0 to 25 deg C

5: (COCl)2, DMSO, DIPEA / CH₂Cl₂

6: BF₃*Et₂O / CH₂Cl₂ / -78 - -20 °C

7: DIPEA / CH₂Cl₂ / 0 °C

8: OsO₄, NMO / acetone; butan-1-ol; H₂O

9: NaIO₄ / tetrahydrofuran; H₂O

10: toluene / 70 °C

11: 85 percent / 8.8 eq. NaBH₄ / methanol

12: DIPEA / CH₂Cl₂

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; Zn(N₃)2/bis-pyridine complex; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone; toluene; butan-1-ol;
DOI:10.1021/jo00062a003

Reference yield:

: 148064-49-7
(R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(3,5-dibenzyl-4-oxo-[1,3,5]triazinan-1-yl)-propionic acid ethyl ester

: 148064-59-9
(2S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(3,5-dibenzyl-4-oxo-[1,3,5]triazinan-1-yl)-2-methoxycarbonylmethyl-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: LiBH₄ / diethyl ether

2: Zn(N₃)2(py)2, Ph₃P, DEAD, imid / toluene

3: H₂ / 10percent Pd/C / ethanol

4: pyridine / CH₂Cl₂

5: TBAF / tetrahydrofuran / 0 to 25 deg C

6: (COCl)2, DMSO, DIPEA / CH₂Cl₂

7: BF₃*Et₂O / CH₂Cl₂ / -78 - -20 °C

8: DIPEA / CH₂Cl₂ / 0 °C

9: OsO₄, NMO / acetone; butan-1-ol; H₂O

10: NaIO₄ / tetrahydrofuran; H₂O

11: toluene / 70 °C

12: 85 percent / 8.8 eq. NaBH₄ / methanol

13: DIPEA / CH₂Cl₂

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium borohydride; N-methyl-2-indolinone; oxalyl dichloride; Zn(N₃)2/bis-pyridine complex; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; toluene; butan-1-ol;
DOI:10.1021/jo00062a003