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

Base Information

Chemical Name:3-[(2S,3R,4R,5R,6R)-3-Allyloxycarbonylamino-6-azidomethyl-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylsulfanyl]-propionic acid
CAS No.:685133-09-9
Molecular Formula:C₂₇H₄₂N₄O₈SSi
Molecular Weight:610.804
Hs Code.:

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

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

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

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

There total 10 articles about 3-[(2S,3R,4R,5R,6R)-3-Allyloxycarbonylamino-6-azidomethyl-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylsulfanyl]-propionic acid 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: 86.0%

: 685133-06-6
3-[(2S,3R,4R,5R,6R)-3-Allyloxycarbonylamino-6-azidomethyl-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylsulfanyl]-propionic acid methyl ester

: 685133-09-9
3-[(2S,3R,4R,5R,6R)-3-Allyloxycarbonylamino-6-azidomethyl-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylsulfanyl]-propionic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 5h;
DOI:10.1002/anie.200352919

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 685133-09-9
3-[(2S,3R,4R,5R,6R)-3-Allyloxycarbonylamino-6-azidomethyl-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylsulfanyl]-propionic acid

Guidance literature:: Multi-step reaction with 6 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

6: 86 percent / aq. LiOH / tetrahydrofuran / 5 h / 20 °C

With pyridine; lithium hydroxide; sodium azide; tetramethylsilane; sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; 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

: 685133-09-9
3-[(2S,3R,4R,5R,6R)-3-Allyloxycarbonylamino-6-azidomethyl-4-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylsulfanyl]-propionic acid

Guidance literature:: Multi-step reaction with 9 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

9: 86 percent / aq. LiOH / tetrahydrofuran / 5 h / 20 °C

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