(3R,4R,5R,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)piperidin-3,4-diol

Base Information

Chemical Name:(3R,4R,5R,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)piperidin-3,4-diol
CAS No.:528821-23-0
Molecular Formula:C₂₆H₃₉NO₄Si
Molecular Weight:457.685
Hs Code.:

Synonyms:(3R,4R,5R,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)piperidin-3,4-diol

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Chemical Property of (3R,4R,5R,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)piperidin-3,4-diol

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Technology Process of (3R,4R,5R,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)piperidin-3,4-diol

There total 8 articles about (3R,4R,5R,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)piperidin-3,4-diol 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%

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

: 528821-23-0
(3R,4R,5R,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)piperidin-3,4-diol

Guidance literature:: With lithium aluminium tetrahydride; In diethyl ether; at 20 ℃; for 3h;
DOI:10.1016/S0040-4020(02)01534-X

Reference yield:

: 100-39-0
benzyl bromide

: 528821-23-0
(3R,4R,5R,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)piperidin-3,4-diol

Guidance literature:: Multi-step reaction with 3 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

3.1: 89 percent / LiAlH₄ / diethyl ether / 3 h / 20 °C

With osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; sodium hydride; In diethyl ether; 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

: 528821-23-0
(3R,4R,5R,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)piperidin-3,4-diol

Guidance literature:: Multi-step reaction with 8 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

8.1: 89 percent / LiAlH₄ / diethyl ether / 3 h / 20 °C

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