4-[(2S,3R,4R,5R,6R)-3-Allyloxycarbonylamino-6-azidomethyl-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylsulfanyl]-butyric acid methyl ester

Base Information

Chemical Name:4-[(2S,3R,4R,5R,6R)-3-Allyloxycarbonylamino-6-azidomethyl-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylsulfanyl]-butyric acid methyl ester
CAS No.:685133-07-7
Molecular Formula:C₂₉H₄₆N₄O₈SSi
Molecular Weight:638.858
Hs Code.:

4-[(2S,3R,4R,5R,6R)-3-Allyloxycarbonylamino-6-azidomethyl-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylsulfanyl]-butyric acid methyl ester

Synonyms:4-[(2S,3R,4R,5R,6R)-3-Allyloxycarbonylamino-6-azidomethyl-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylsulfanyl]-butyric acid methyl ester

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Chemical Property of 4-[(2S,3R,4R,5R,6R)-3-Allyloxycarbonylamino-6-azidomethyl-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylsulfanyl]-butyric acid methyl ester

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Technology Process of 4-[(2S,3R,4R,5R,6R)-3-Allyloxycarbonylamino-6-azidomethyl-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylsulfanyl]-butyric acid methyl ester

There total 9 articles about 4-[(2S,3R,4R,5R,6R)-3-Allyloxycarbonylamino-6-azidomethyl-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylsulfanyl]-butyric acid methyl ester 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:

: 4-[(2S,3R,4R,5R,6R)-3-Allyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-methanesulfonyloxymethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylsulfanyl]-butyric acid methyl ester

: 685133-07-7
4-[(2S,3R,4R,5R,6R)-3-Allyloxycarbonylamino-6-azidomethyl-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylsulfanyl]-butyric acid methyl ester

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 75 ℃;
DOI:10.1002/anie.200352919

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 685133-07-7
4-[(2S,3R,4R,5R,6R)-3-Allyloxycarbonylamino-6-azidomethyl-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylsulfanyl]-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: TsOH / dimethylformamide / 6 h / 50 °C / 15 Torr

2: pyridine / CH₂Cl₂ / 4 h / 0 - 20 °C

3: NaBH₃CN; TMS / acetonitrile / 12 h / 0 - 20 °C

4: pyridine / CH₂Cl₂ / 6 h / 0 - 20 °C

5: NaN₃ / dimethylformamide / 75 °C

With pyridine; sodium azide; tetramethylsilane; sodium cyanoborohydride; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/anie.200352919

Reference yield:

: 146934-02-3
2-N-Allyloxycarbonyl-2-amino-2-deoxy-D-glucopyranose

: 685133-07-7
4-[(2S,3R,4R,5R,6R)-3-Allyloxycarbonylamino-6-azidomethyl-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylsulfanyl]-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: pyridine / 12 h / 20 °C

2: BF₃*Et₂O / CH₂Cl₂ / 12 h / 20 °C

3: 100 percent / MeONa / methanol / 4 h / 20 °C

4: TsOH / dimethylformamide / 6 h / 50 °C / 15 Torr

5: pyridine / CH₂Cl₂ / 4 h / 0 - 20 °C

6: NaBH₃CN; TMS / acetonitrile / 12 h / 0 - 20 °C

7: pyridine / CH₂Cl₂ / 6 h / 0 - 20 °C

8: NaN₃ / dimethylformamide / 75 °C

With pyridine; sodium azide; tetramethylsilane; boron trifluoride diethyl etherate; sodium methylate; sodium cyanoborohydride; toluene-4-sulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/anie.200352919