5-(benzyl-benzyloxy-amino)-4-{hydroxy-[3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-methyl}-6-phenylsulfanyl-2-trimethylsilanyloxymethyl-tetrahydro-pyran-3-ol

Base Information

Chemical Name:5-(benzyl-benzyloxy-amino)-4-{hydroxy-[3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-methyl}-6-phenylsulfanyl-2-trimethylsilanyloxymethyl-tetrahydro-pyran-3-ol
CAS No.:328386-14-7
Molecular Formula:C₆₀H₁₀₅NO₁₀SSi₅
Molecular Weight:1172.99
Hs Code.:

5-(benzyl-benzyloxy-amino)-4-{hydroxy-[3,4,5-tris-(<i>tert</i>-butyl-dimethyl-silanyloxy)-6-(<i>tert</i>-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-methyl}-6-phenylsulfanyl-2-trimethylsilanyloxymethyl-tetrahydro-pyran-3-ol

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Chemical Property of 5-(benzyl-benzyloxy-amino)-4-{hydroxy-[3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-methyl}-6-phenylsulfanyl-2-trimethylsilanyloxymethyl-tetrahydro-pyran-3-ol

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Technology Process of 5-(benzyl-benzyloxy-amino)-4-{hydroxy-[3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-methyl}-6-phenylsulfanyl-2-trimethylsilanyloxymethyl-tetrahydro-pyran-3-ol

There total 10 articles about 5-(benzyl-benzyloxy-amino)-4-{hydroxy-[3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-methyl}-6-phenylsulfanyl-2-trimethylsilanyloxymethyl-tetrahydro-pyran-3-ol 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: 53.0%

: 4551-15-9
phenylthiotrimethylsilane

: 328386-13-6
(1R,2R,3R,4R,5R)-4-(Benzyl-benzyloxy-amino)-3-{(R)-hydroxy-[(2S,3S,4S,5S,6R)-3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-methyl}-6,8-dioxa-bicyclo[3.2.1]octan-2-ol

: 328386-14-7
5-(benzyl-benzyloxy-amino)-4-{hydroxy-[3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-methyl}-6-phenylsulfanyl-2-trimethylsilanyloxymethyl-tetrahydro-pyran-3-ol

Guidance literature:: With zinc(II) iodide;
DOI:10.1055/s-2001-9698

Reference yield:

: 4383-24-8
N,O-dibenzylhydroxylamine

: 328386-14-7
5-(benzyl-benzyloxy-amino)-4-{hydroxy-[3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-methyl}-6-phenylsulfanyl-2-trimethylsilanyloxymethyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 41 percent / Me₂AlCl / -78 - -15 °C

2: 70 percent / LiBH₄ / tetrahydrofuran / -78 - -15 °C

3: 53 percent / ZnI₂

With lithium borohydride; dimethylaluminum chloride; zinc(II) iodide; In tetrahydrofuran;
DOI:10.1055/s-2001-9698

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 328386-14-7
5-(benzyl-benzyloxy-amino)-4-{hydroxy-[3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-methyl}-6-phenylsulfanyl-2-trimethylsilanyloxymethyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1: pyridine; DMAP

2: O₃ / CH₂Cl₂ / -78 °C

3: 61 percent / Et₂AlI / toluene; CH₂Cl₂ / 2 h / -78 °C

4: 41 percent / Me₂AlCl / -78 - -15 °C

5: 70 percent / LiBH₄ / tetrahydrofuran / -78 - -15 °C

6: 53 percent / ZnI₂

With pyridine; dmap; lithium borohydride; dimethylaluminum chloride; diethylaluminum iodide; ozone; zinc(II) iodide; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1055/s-2001-9698