(3S,4R,5R,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)-3,4-dihydroxy-piperidin-2-one

Base Information

Chemical Name:(3S,4R,5R,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)-3,4-dihydroxy-piperidin-2-one
CAS No.:528821-15-0
Molecular Formula:C₂₆H₃₇NO₅Si
Molecular Weight:471.669
Hs Code.:

Synonyms:(3S,4R,5R,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)-3,4-dihydroxy-piperidin-2-one

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Chemical Property of (3S,4R,5R,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)-3,4-dihydroxy-piperidin-2-one

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Technology Process of (3S,4R,5R,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)-3,4-dihydroxy-piperidin-2-one

There total 7 articles about (3S,4R,5R,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)-3,4-dihydroxy-piperidin-2-one 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: 89.0%

: 528821-13-8
(5S,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)-5,6-dihydro-1H-pyridin-2-one

: 528821-15-0
(3S,4R,5R,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)-3,4-dihydroxy-piperidin-2-one

: (3R,4S,5R,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)-3,4-dihydroxy-piperidin-2-one

Guidance literature:: With osmium(VIII) oxide; N-methyl-2-indolinone; In water; tert-butyl alcohol; at 20 ℃; for 3h;
DOI:10.1016/S0040-4020(02)01534-X

Reference yield:

: 100-39-0
benzyl bromide

: 528821-15-0
(3S,4R,5R,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)-3,4-dihydroxy-piperidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: NaH / dimethylformamide / 0.5 h / 0 °C

1.2: 64 percent / dimethylformamide / 0 - 20 °C

2.1: 89 percent / NMO; osmium tetroxide / 2-methyl-propan-2-ol; H₂O / 3 h / 20 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; sodium hydride; In water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1016/S0040-4020(02)01534-X

Reference yield:

: 124085-68-3
tert-butyl (R)-1-(tert-butyldimethylsilyloxy)-3-oxopropan-2-yl carbamate

: 528821-15-0
(3S,4R,5R,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)-3,4-dihydroxy-piperidin-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: tetrahydrofuran / -78 - 20 °C

2.1: 7.23 g / potassium tert-butoxide / tetrahydrofuran / 3 h / 20 °C

3.1: 81 percent / PdCl₂(PPh₃)2 / ethanol / 32 h / 60 °C / 45600 Torr

4.1: 76 percent / NaHCO₃; Oxone / acetone; H₂O / 3 h / 20 °C

5.1: 95 percent / DBU / CH₂Cl₂ / 3 h / Heating

6.1: NaH / dimethylformamide / 0.5 h / 0 °C

6.2: 64 percent / dimethylformamide / 0 - 20 °C

7.1: 89 percent / NMO; osmium tetroxide / 2-methyl-propan-2-ol; H₂O / 3 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; Oxone; osmium(VIII) oxide; N-methyl-2-indolinone; potassium tert-butylate; sodium hydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1016/S0040-4020(02)01534-X