(2S,3S,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-3,6-dihydro-2H-pyran-3-ol

Base Information

Chemical Name:(2S,3S,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-3,6-dihydro-2H-pyran-3-ol
CAS No.:158347-51-4
Molecular Formula:C₂₃H₃₀O₄Si
Molecular Weight:398.574
Hs Code.:

Synonyms:(2S,3S,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-3,6-dihydro-2H-pyran-3-ol

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Chemical Property of (2S,3S,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-3,6-dihydro-2H-pyran-3-ol

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Technology Process of (2S,3S,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-3,6-dihydro-2H-pyran-3-ol

There total 7 articles about (2S,3S,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-3,6-dihydro-2H-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: 97.0%

: 198057-24-8
tert-Butyl-[(2S,3S,6R)-6-methoxy-3-(4-methoxy-benzyloxy)-3,6-dihydro-2H-pyran-2-ylmethoxy]-diphenyl-silane

: 158347-51-4
(2S,3S,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-3,6-dihydro-2H-pyran-3-ol

Guidance literature:: With phosphate buffer; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; for 1h; Ambient temperature;
DOI:10.1248/cpb.45.1558

Reference yield:

: 198057-20-4
(3S,4S)-1,1-dibromo-3-(4-methoxybenzyloxy)-4,5-pentylidenedioxy-1-pentene

: 158347-51-4
(2S,3S,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-3,6-dihydro-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) N-BuLi / 1.) n-hexane, THF, -78 deg C, 1 h, 2.) n-hexane, THF, from -78 deg C, 30 min to RT, 1 h

2: 90 percent / H₂, quinoline / 5percent Pd/BaSO₄ / ethyl acetate / 0.25 h

3: 98 percent / 1N aq. HCl / methanol / 2 h / Ambient temperature

4: 96 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

5: 95 percent / TsOH*H₂O / benzene / 17 h / Ambient temperature

6: 1.) DIBAH, 2.) dl-CSA / 1.) n-hexane, toluene, -78 deg C, 1 h, 2.) RT, 30 min

7: 97 percent / DDQ, phosphate buffer / methanol / 1 h / Ambient temperature

With 1H-imidazole; quinoline; hydrogenchloride; n-butyllithium; phosphate buffer; DL-10-camphorsulfonic acid; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Pd-BaSO₄; In methanol; dichloromethane; ethyl acetate; benzene;
DOI:10.1248/cpb.45.1558

Reference yield:

: 198057-21-5
(S)-4-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-but-2-ynoic acid methyl ester

: 158347-51-4
(2S,3S,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-3,6-dihydro-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / H₂, quinoline / 5percent Pd/BaSO₄ / ethyl acetate / 0.25 h

2: 98 percent / 1N aq. HCl / methanol / 2 h / Ambient temperature

3: 96 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

4: 95 percent / TsOH*H₂O / benzene / 17 h / Ambient temperature

5: 1.) DIBAH, 2.) dl-CSA / 1.) n-hexane, toluene, -78 deg C, 1 h, 2.) RT, 30 min

6: 97 percent / DDQ, phosphate buffer / methanol / 1 h / Ambient temperature

With 1H-imidazole; quinoline; hydrogenchloride; phosphate buffer; DL-10-camphorsulfonic acid; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Pd-BaSO₄; In methanol; dichloromethane; ethyl acetate; benzene;
DOI:10.1248/cpb.45.1558