tert-Butyl-((2S,3S,4R,6S)-2,3-dimethoxy-6-trityloxymethyl-tetrahydro-pyran-4-yloxy)-dimethyl-silane

Base Information

Chemical Name:tert-Butyl-((2S,3S,4R,6S)-2,3-dimethoxy-6-trityloxymethyl-tetrahydro-pyran-4-yloxy)-dimethyl-silane
CAS No.:78462-66-5
Molecular Formula:C₃₃H₄₄O₅Si
Molecular Weight:548.795
Hs Code.:

Synonyms:tert-Butyl-((2S,3S,4R,6S)-2,3-dimethoxy-6-trityloxymethyl-tetrahydro-pyran-4-yloxy)-dimethyl-silane

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Chemical Property of tert-Butyl-((2S,3S,4R,6S)-2,3-dimethoxy-6-trityloxymethyl-tetrahydro-pyran-4-yloxy)-dimethyl-silane

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Technology Process of tert-Butyl-((2S,3S,4R,6S)-2,3-dimethoxy-6-trityloxymethyl-tetrahydro-pyran-4-yloxy)-dimethyl-silane

There total 10 articles about tert-Butyl-((2S,3S,4R,6S)-2,3-dimethoxy-6-trityloxymethyl-tetrahydro-pyran-4-yloxy)-dimethyl-silane 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:

: 617-04-9
(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

: 78462-66-5
tert-Butyl-((2S,3S,4R,6S)-2,3-dimethoxy-6-trityloxymethyl-tetrahydro-pyran-4-yloxy)-dimethyl-silane

Guidance literature:: Multi-step reaction with 8 steps

1: 47.1 percent / pyridinium p-toluenesulfonate / acetone; dimethylformamide / 36 h / 5 °C

2: 53.2 g / CH₂Cl₂; pyridine / 60 h

3: 60 percent / NaH / tetrahydrofuran / 1.5 h / Ambient temperature

4: 100 percent / Dowex 50W (H+) / methanol / 3.5 h / Ambient temperature

5: 86 percent / pyridine / 1.5 h / 70 °C

6: 86 percent / t-BuOK / tetrahydrofuran / 0.5 h / 0 °C

7: LiBEt₃H / tetrahydrofuran / 120 h / -20 °C

8: imidazole / dimethylformamide / 6 h / 75 °C

With 1H-imidazole; Dowex 50W (H+); potassium tert-butylate; sodium hydride; lithium triethylborohydride; pyridinium p-toluenesulfonate; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ja00323a032

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 78462-65-4
(2S,3S,4R,6S)-2,3-Dimethoxy-6-trityloxymethyl-tetrahydro-pyran-4-ol

: 78462-66-5
tert-Butyl-((2S,3S,4R,6S)-2,3-dimethoxy-6-trityloxymethyl-tetrahydro-pyran-4-yloxy)-dimethyl-silane

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 75 ℃; for 6h; Yield given;
DOI:10.1021/ja00323a032

Reference yield:

: 63167-67-9
methyl 4,6-O-isopropylidene-α-D-mannopyranoside

: 78462-66-5
tert-Butyl-((2S,3S,4R,6S)-2,3-dimethoxy-6-trityloxymethyl-tetrahydro-pyran-4-yloxy)-dimethyl-silane

Guidance literature:: Multi-step reaction with 7 steps

1: 53.2 g / CH₂Cl₂; pyridine / 60 h

2: 60 percent / NaH / tetrahydrofuran / 1.5 h / Ambient temperature

3: 100 percent / Dowex 50W (H+) / methanol / 3.5 h / Ambient temperature

4: 86 percent / pyridine / 1.5 h / 70 °C

5: 86 percent / t-BuOK / tetrahydrofuran / 0.5 h / 0 °C

6: LiBEt₃H / tetrahydrofuran / 120 h / -20 °C

7: imidazole / dimethylformamide / 6 h / 75 °C

With 1H-imidazole; Dowex 50W (H+); potassium tert-butylate; sodium hydride; lithium triethylborohydride; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00323a032