(2R,3S,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-3,4-diol

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Chemical Name:(2R,3S,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-3,4-diol
CAS No.:220774-98-1
Molecular Formula:C₃₈H₄₆O₅SSi
Molecular Weight:642.932
Hs Code.:

Synonyms:(2R,3S,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-3,4-diol

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Chemical Property of (2R,3S,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-3,4-diol

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Technology Process of (2R,3S,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-3,4-diol

There total 4 articles about (2R,3S,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-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: 90.0%

: 220774-94-7
phenyl 3-O-TBDMS-4-C-methyl-6-O-trityl-1-thio-β-D-glucopyranoside

: 220774-98-1
(2R,3S,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-3,4-diol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.25h; Ambient temperature;
DOI:10.1016/S0040-4039(98)80003-8

Reference yield:

: 220774-88-9
(2S,3R,4S,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-phenylsulfanyl-6-trityloxymethyl-tetrahydro-pyran-3,5-diol

: 220774-98-1
(2R,3S,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-3,4-diol

Guidance literature:: Multi-step reaction with 4 steps

1: pyridine, DMAP / 1 h / 0 - 10 °C

2: 75 percent / PDC, Ac₂O / CH₂Cl₂ / 2 h / Heating

3: CeCl₃ / toluene / -76 deg C -> r.t., 14 h

4: 90 percent / TBAF / tetrahydrofuran / 0.25 h / Ambient temperature

With pyridine; dmap; dipyridinium dichromate; cerium(III) chloride; tetrabutyl ammonium fluoride; acetic anhydride; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1016/S0040-4039(98)80003-8

Reference yield:

: 220774-92-5
Acetic acid (2S,3R,4R,6R)-4-(tert-butyl-dimethyl-silanyloxy)-5-oxo-2-phenylsulfanyl-6-trityloxymethyl-tetrahydro-pyran-3-yl ester

: 220774-98-1
(2R,3S,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-3,4-diol

Guidance literature:: Multi-step reaction with 2 steps

1: CeCl₃ / toluene / -76 deg C -> r.t., 14 h

2: 90 percent / TBAF / tetrahydrofuran / 0.25 h / Ambient temperature

With cerium(III) chloride; tetrabutyl ammonium fluoride; In tetrahydrofuran; toluene;
DOI:10.1016/S0040-4039(98)80003-8