(2R,3S,4S,5R,6R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-6-[(S)-3-(4-methoxy-benzyloxy)-1-methyl-propoxy]-tetrahydro-pyran-3,4,5-triol

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Chemical Name:(2R,3S,4S,5R,6R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-6-[(S)-3-(4-methoxy-benzyloxy)-1-methyl-propoxy]-tetrahydro-pyran-3,4,5-triol
CAS No.:184648-44-0
Molecular Formula:C₂₄H₄₂O₈Si
Molecular Weight:486.678
Hs Code.:

Synonyms:(2R,3S,4S,5R,6R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-6-[(S)-3-(4-methoxy-benzyloxy)-1-methyl-propoxy]-tetrahydro-pyran-3,4,5-triol

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Chemical Property of (2R,3S,4S,5R,6R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-6-[(S)-3-(4-methoxy-benzyloxy)-1-methyl-propoxy]-tetrahydro-pyran-3,4,5-triol

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Technology Process of (2R,3S,4S,5R,6R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-6-[(S)-3-(4-methoxy-benzyloxy)-1-methyl-propoxy]-tetrahydro-pyran-3,4,5-triol

There total 5 articles about (2R,3S,4S,5R,6R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-6-[(S)-3-(4-methoxy-benzyloxy)-1-methyl-propoxy]-tetrahydro-pyran-3,4,5-triol 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:

: 81058-27-7
2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide

: 184648-44-0
(2R,3S,4S,5R,6R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-6-[(S)-3-(4-methoxy-benzyloxy)-1-methyl-propoxy]-tetrahydro-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 6 steps

1: 83 percent / 4 Angstroem molecular sieves, Ag₂CO₃ / diethyl ether / 48 h

2: 95 percent / H₂ / Pd-C / methanol / 5 h

3: 93 percent / BF₃*THF / tetrahydrofuran / 1) 0 deg C, 30 min, 2) 0 deg C -> room temperature, 30 min

4: TfOH / diethyl ether / 2 h / Ambient temperature

5: 2.39 g / NaOH / H₂O; ethanol / 36 h

6: 92 percent / imidazole / CH₂Cl₂ / 24 h / 0 °C

With 1H-imidazole; sodium hydroxide; boron trifluoride-tetrahydrofuran complex; trifluorormethanesulfonic acid; 4 A molecular sieve; hydrogen; silver carbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water;
DOI:10.1021/jo961623r

Reference yield:

: 184648-40-6
(S)-3-[(2R,3R,4S,5R,6R)-3,4,5-Tris-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-2-yloxy]-butyric acid benzyl ester

: 184648-44-0
(2R,3S,4S,5R,6R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-6-[(S)-3-(4-methoxy-benzyloxy)-1-methyl-propoxy]-tetrahydro-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / H₂ / Pd-C / methanol / 5 h

2: 93 percent / BF₃*THF / tetrahydrofuran / 1) 0 deg C, 30 min, 2) 0 deg C -> room temperature, 30 min

3: TfOH / diethyl ether / 2 h / Ambient temperature

4: 2.39 g / NaOH / H₂O; ethanol / 36 h

5: 92 percent / imidazole / CH₂Cl₂ / 24 h / 0 °C

With 1H-imidazole; sodium hydroxide; boron trifluoride-tetrahydrofuran complex; trifluorormethanesulfonic acid; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water;
DOI:10.1021/jo961623r

Reference yield:

: 184648-42-8
2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-((S)-3-hydroxy-1-methyl-propoxy)-tetrahydro-pyran-4-yl ester

: 184648-44-0
(2R,3S,4S,5R,6R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-6-[(S)-3-(4-methoxy-benzyloxy)-1-methyl-propoxy]-tetrahydro-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 3 steps

1: TfOH / diethyl ether / 2 h / Ambient temperature

2: 2.39 g / NaOH / H₂O; ethanol / 36 h

3: 92 percent / imidazole / CH₂Cl₂ / 24 h / 0 °C

With 1H-imidazole; sodium hydroxide; trifluorormethanesulfonic acid; In diethyl ether; ethanol; dichloromethane; water;
DOI:10.1021/jo961623r