(2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-2-(tert-butyldimethylsilyloxymethyl)-6-methoxy-1-(toluene-4-sulfonyl)piperidine

Base Information

Chemical Name:(2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-2-(tert-butyldimethylsilyloxymethyl)-6-methoxy-1-(toluene-4-sulfonyl)piperidine
CAS No.:475976-15-9
Molecular Formula:C₄₁H₅₃NO₇SSi
Molecular Weight:732.026
Hs Code.:

Synonyms:(2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-2-(tert-butyldimethylsilyloxymethyl)-6-methoxy-1-(toluene-4-sulfonyl)piperidine

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Chemical Property of (2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-2-(tert-butyldimethylsilyloxymethyl)-6-methoxy-1-(toluene-4-sulfonyl)piperidine

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Technology Process of (2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-2-(tert-butyldimethylsilyloxymethyl)-6-methoxy-1-(toluene-4-sulfonyl)piperidine

There total 6 articles about (2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-2-(tert-butyldimethylsilyloxymethyl)-6-methoxy-1-(toluene-4-sulfonyl)piperidine 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: 91.0%

: 100-39-0
benzyl bromide

: 475976-14-8
(2R,3S,4R,5R,6S)-5-benzyloxy-6-(tert-butyldimethylsilyloxymethyl)-2-methoxy-1-(toluene-4-sulfonyl)piperidine-3,4-diol

: 475976-15-9
(2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-2-(tert-butyldimethylsilyloxymethyl)-6-methoxy-1-(toluene-4-sulfonyl)piperidine

Guidance literature:: (2R,3S,4R,5R,6S)-5-benzyloxy-6-(tert-butyldimethylsilyloxymethyl)-2-methoxy-1-(toluene-4-sulfonyl)piperidine-3,4-diol; With sodium hydride; In tetrahydrofuran; at 0 - 15 ℃; for 0.75h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 15 ℃; for 2h;
DOI:10.1055/s-2002-33706

Reference yield:

: 100-39-0
benzyl bromide

: 475976-15-9
(2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-2-(tert-butyldimethylsilyloxymethyl)-6-methoxy-1-(toluene-4-sulfonyl)piperidine

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

1.2: 91 percent / Bu₄NI / tetrahydrofuran / 2 h / 20 °C

2.1: 96 percent / OsO₄; NMO / acetone; 2-methyl-propan-2-ol / 6 h

3.1: NaH / tetrahydrofuran / 0.75 h / 0 - 15 °C

3.2: 91 percent / Bu₄NI / tetrahydrofuran / 2 h / 15 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; sodium hydride; In tetrahydrofuran; acetone; tert-butyl alcohol;
DOI:10.1055/s-2002-33706

Reference yield:

: 475976-10-4
(2S,6R)-2-(tert-butyl-dimethyl-siloxymethyl)-6-hydroxy-1-(toluene-4-sulfonyl)-1,6-dihydro-2H-pyridin-3-one

: 475976-15-9
(2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-2-(tert-butyldimethylsilyloxymethyl)-6-methoxy-1-(toluene-4-sulfonyl)piperidine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 94 percent / BF₃*Et₂O; molecular sieves 4 Angstroem / 3 h / 0 °C

2.1: 89 percent / NaBH₄; CeCl₃*7H₂O / methanol / 0.67 h / -30 °C

3.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

3.2: 91 percent / Bu₄NI / tetrahydrofuran / 2 h / 20 °C

4.1: 96 percent / OsO₄; NMO / acetone; 2-methyl-propan-2-ol / 6 h

5.1: NaH / tetrahydrofuran / 0.75 h / 0 - 15 °C

5.2: 91 percent / Bu₄NI / tetrahydrofuran / 2 h / 15 °C

With sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; cerium(III) chloride; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium hydride; In tetrahydrofuran; methanol; acetone; tert-butyl alcohol;
DOI:10.1055/s-2002-33706