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

Base Information

Chemical Name:(2R,3S,4R,5R,6S)-5-benzyloxy-6-(tert-butyldimethylsilyloxymethyl)-2-methoxy-1-(toluene-4-sulfonyl)piperidine-3,4-diol
CAS No.:475976-14-8
Molecular Formula:C₂₇H₄₁NO₇SSi
Molecular Weight:551.777
Hs Code.:

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

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

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

There total 5 articles about (2R,3S,4R,5R,6S)-5-benzyloxy-6-(tert-butyldimethylsilyloxymethyl)-2-methoxy-1-(toluene-4-sulfonyl)piperidine-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: 96.0%

: 475976-13-7
(2S,3S,6R)-3-benzyloxy-2-(tert-butyl-dimethyl-siloxymethyl)-6-methoxy-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydro-pyridine

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

Guidance literature:: With osmium(VIII) oxide; N-methyl-2-indolinone; In acetone; tert-butyl alcohol; for 6h;
DOI:10.1055/s-2002-33706

Reference yield:

: 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

Guidance literature:: Multi-step reaction with 2 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

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

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

Guidance literature:: Multi-step reaction with 4 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

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