N-[(1R,3S,4S,5R,6S)-3-O-{tert-butyl(dimethyl)silyloxy}-6-({tert-butyl(dimethyl)silyloxy}methyl)-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexyl]-N-benzylamine

Base Information

Chemical Name:N-[(1R,3S,4S,5R,6S)-3-O-{tert-butyl(dimethyl)silyloxy}-6-({tert-butyl(dimethyl)silyloxy}methyl)-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexyl]-N-benzylamine
CAS No.:498539-42-7
Molecular Formula:C₂₉H₅₃NO₄Si₂
Molecular Weight:535.915
Hs Code.:

N-[(1R,3S,4S,5R,6S)-3-O-{tert-butyl(dimethyl)silyloxy}-6-({tert-butyl(dimethyl)silyloxy}methyl)-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexyl]-N-benzylamine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of N-[(1R,3S,4S,5R,6S)-3-O-{tert-butyl(dimethyl)silyloxy}-6-({tert-butyl(dimethyl)silyloxy}methyl)-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexyl]-N-benzylamine

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Technology Process of N-[(1R,3S,4S,5R,6S)-3-O-{tert-butyl(dimethyl)silyloxy}-6-({tert-butyl(dimethyl)silyloxy}methyl)-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexyl]-N-benzylamine

There total 6 articles about N-[(1R,3S,4S,5R,6S)-3-O-{tert-butyl(dimethyl)silyloxy}-6-({tert-butyl(dimethyl)silyloxy}methyl)-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexyl]-N-benzylamine 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:

: Benzyl-[(3aR,4R,7S,7aS)-7-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-benzo[1,3]dioxol-(5E)-ylidene]-amine

: 498539-42-7
N-[(1R,3S,4S,5R,6S)-3-O-{tert-butyl(dimethyl)silyloxy}-6-({tert-butyl(dimethyl)silyloxy}methyl)-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexyl]-N-benzylamine

: N-[(1S,3S,4S,5R,6S)-3-O-{tert-butyl(dimethyl)silyloxy}-6-({tert-butyl(dimethyl)silyloxy}methyl)-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexyl]-N-benzylamine

Guidance literature:: With sodium cyanoborohydride; In ethanol; at 20 ℃; for 14h;
DOI:10.1016/j.tet.2003.09.049

Reference yield:

: 100-46-9
benzylamine

: 498539-40-5
[3S,4S,5R,6R]-3-O-tert-butyl(dimethyl)silyl-6-tert-butyl(dimethyl)silyloxymethyl-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexan-1-one

: 498539-42-7
N-[(1R,3S,4S,5R,6S)-3-O-{tert-butyl(dimethyl)silyloxy}-6-({tert-butyl(dimethyl)silyloxy}methyl)-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexyl]-N-benzylamine

: N-[(1S,3S,4S,5R,6S)-3-O-{tert-butyl(dimethyl)silyloxy}-6-({tert-butyl(dimethyl)silyloxy}methyl)-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexyl]-N-benzylamine

Guidance literature:: benzylamine; [3S,4S,5R,6R]-3-O-tert-butyl(dimethyl)silyl-6-tert-butyl(dimethyl)silyloxymethyl-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexan-1-one; With titanium(IV) isopropylate; at 20 ℃; for 2h;

With sodium cyanoborohydride; In ethanol; at 20 ℃; for 12h;
DOI:10.1016/S0040-4039(02)02016-6

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 498539-42-7
N-[(1R,3S,4S,5R,6S)-3-O-{tert-butyl(dimethyl)silyloxy}-6-({tert-butyl(dimethyl)silyloxy}methyl)-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexyl]-N-benzylamine

Guidance literature:: Multi-step reaction with 4 steps

1: 88 percent / imidazole / dimethylformamide / 24 h / 70 °C

2: 77 percent / N-bromosuccinimide / acetone; H₂O / 0.5 h / -25 °C

3: Ti(OiPr)4 / ethanol / 2 h / 20 °C

4: sodium cyanoborohydride / ethanol / 14 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; N-Bromosuccinimide; sodium cyanoborohydride; In ethanol; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/j.tet.2003.09.049