(2S,3S,4S,6S)-2-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol

Base Information

Chemical Name:(2S,3S,4S,6S)-2-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol
CAS No.:693807-23-7
Molecular Formula:C₃₇H₄₄O₆Si
Molecular Weight:612.838
Hs Code.:

Synonyms:(2S,3S,4S,6S)-2-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol

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Chemical Property of (2S,3S,4S,6S)-2-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol

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Technology Process of (2S,3S,4S,6S)-2-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol

There total 7 articles about (2S,3S,4S,6S)-2-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-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: 93.0%

: 824-94-2
p-methoxybenzyl chloride

: 693807-21-5
(2S,3S,4S,6S)-2-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3,4-diol

: 693807-23-7
(2S,3S,4S,6S)-2-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol

Guidance literature:: (2S,3S,4S,6S)-2-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3,4-diol; With di(n-butyl)tin oxide; In methanol; for 2h; Heating;

p-methoxybenzyl chloride; With cesium fluoride; sodium iodide; In methanol; N,N-dimethyl-formamide; at 20 ℃; for 24h; Further stages.;
DOI:10.1016/j.tetlet.2004.02.106

Reference yield:

: 15548-45-5
(2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

: 693807-23-7
(2S,3S,4S,6S)-2-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: imidazole / dimethylformamide / 20 °C

2.1: CSA / acetone

3.1: NaHMDS / tetrahydrofuran / 0.33 h / -78 °C

3.2: 100 percent / tetrahydrofuran / -78 - 20 °C

4.1: 84 percent / Bu₃SnH; AIBN / toluene / 90 °C

5.1: 78 percent / AcOH; H₂O / 2 h / 80 °C

6.1: Bu₂SnO / methanol / 2 h / Heating

6.2: 93 percent / CsF; NaI / dimethylformamide; methanol / 24 h / 20 °C

With 1H-imidazole; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; water; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; di(n-butyl)tin oxide; acetic acid; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1016/j.tetlet.2004.02.106

Reference yield:

: 114894-82-5
benzyl 6-O-tetra-butyldiphenylsilyl-α-D-mannopyranoside

: 693807-23-7
(2S,3S,4S,6S)-2-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: CSA / acetone

2.1: NaHMDS / tetrahydrofuran / 0.33 h / -78 °C

2.2: 100 percent / tetrahydrofuran / -78 - 20 °C

3.1: 84 percent / Bu₃SnH; AIBN / toluene / 90 °C

4.1: 78 percent / AcOH; H₂O / 2 h / 80 °C

5.1: Bu₂SnO / methanol / 2 h / Heating

5.2: 93 percent / CsF; NaI / dimethylformamide; methanol / 24 h / 20 °C

With 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; water; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; di(n-butyl)tin oxide; acetic acid; In tetrahydrofuran; methanol; acetone; toluene;
DOI:10.1016/j.tetlet.2004.02.106