prop-2-enyl (3R,5S,7S,9S,11S,15R)-7-benzyloxy-3-tert-butyldimethylsilyloxy-5,9-epoxy-11,15-epoxy-16-hydroxy-13-[(Z)-2-triisopropylsilyloxyethylidene]-9-methoxy-8,8-dimethylhexadecanoate

Base Information

Chemical Name:prop-2-enyl (3R,5S,7S,9S,11S,15R)-7-benzyloxy-3-tert-butyldimethylsilyloxy-5,9-epoxy-11,15-epoxy-16-hydroxy-13-[(Z)-2-triisopropylsilyloxyethylidene]-9-methoxy-8,8-dimethylhexadecanoate
CAS No.:1314757-00-0
Molecular Formula:C₄₆H₈₀O₉Si₂
Molecular Weight:833.307
Hs Code.:

prop-2-enyl (3R,5S,7S,9S,11S,15R)-7-benzyloxy-3-tert-butyldimethylsilyloxy-5,9-epoxy-11,15-epoxy-16-hydroxy-13-[(Z)-2-triisopropylsilyloxyethylidene]-9-methoxy-8,8-dimethylhexadecanoate

Synonyms:prop-2-enyl (3R,5S,7S,9S,11S,15R)-7-benzyloxy-3-tert-butyldimethylsilyloxy-5,9-epoxy-11,15-epoxy-16-hydroxy-13-[(Z)-2-triisopropylsilyloxyethylidene]-9-methoxy-8,8-dimethylhexadecanoate

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Chemical Property of prop-2-enyl (3R,5S,7S,9S,11S,15R)-7-benzyloxy-3-tert-butyldimethylsilyloxy-5,9-epoxy-11,15-epoxy-16-hydroxy-13-[(Z)-2-triisopropylsilyloxyethylidene]-9-methoxy-8,8-dimethylhexadecanoate

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Technology Process of prop-2-enyl (3R,5S,7S,9S,11S,15R)-7-benzyloxy-3-tert-butyldimethylsilyloxy-5,9-epoxy-11,15-epoxy-16-hydroxy-13-[(Z)-2-triisopropylsilyloxyethylidene]-9-methoxy-8,8-dimethylhexadecanoate

There total 17 articles about prop-2-enyl (3R,5S,7S,9S,11S,15R)-7-benzyloxy-3-tert-butyldimethylsilyloxy-5,9-epoxy-11,15-epoxy-16-hydroxy-13-[(Z)-2-triisopropylsilyloxyethylidene]-9-methoxy-8,8-dimethylhexadecanoate 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: 72.0%

: 1314756-98-3
prop-2-enyl (3R,5S,7S,9S,11S,15R)-7-benzyloxy-3-tert-butyldimethylsilyloxy-5,9-epoxy-11,15-epoxy-13-[(Z)-2-triisopropylsilyloxyethylidene]-9-methoxy-16-(4-methoxybenzyloxy)-8,8-dimethylhexadecanoate

: 1314757-00-0
prop-2-enyl (3R,5S,7S,9S,11S,15R)-7-benzyloxy-3-tert-butyldimethylsilyloxy-5,9-epoxy-11,15-epoxy-16-hydroxy-13-[(Z)-2-triisopropylsilyloxyethylidene]-9-methoxy-8,8-dimethylhexadecanoate

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; at 20 ℃; for 2h;
DOI:10.1039/c1cc12332g

Reference yield:

: 1314756-90-5
dimethyl (4S)-4-benzyloxy-5-[(4R,6S)-6-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxan-4-yl]-3,3-dimethyl-2-oxopentylphosphonate

: 1314757-00-0
prop-2-enyl (3R,5S,7S,9S,11S,15R)-7-benzyloxy-3-tert-butyldimethylsilyloxy-5,9-epoxy-11,15-epoxy-16-hydroxy-13-[(Z)-2-triisopropylsilyloxyethylidene]-9-methoxy-8,8-dimethylhexadecanoate

Guidance literature:: Multi-step reaction with 9 steps

1: 0.8H₂O*BaH₂O₂ / tetrahydrofuran; water / 16 h / 0 - 20 °C

2: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 0.42 h / 0 °C

3: potassium tert-butylate / tetrahydrofuran / 0.08 h / 20 °C

4: pyridine; Dess-Martin periodane / dichloromethane / 1 h / 20 °C

5: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene; water / tetrahydrofuran; tert-butyl alcohol / 1 h / 20 °C

6: sodium hydrogencarbonate / N,N-dimethyl-formamide / 16 h / 70 °C

7: pyridinium p-toluenesulfonate / methanol; dichloromethane / 1 h / 20 °C

8: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 °C

9: 2,3-dicyano-5,6-dichloro-p-benzoquinone / methanol; dichloromethane / 2 h / 20 °C

With pyridine; 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; 0.8H₂O*BaH₂O₂; potassium tert-butylate; water; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; pyridine hydrogenfluoride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 4: Dess-Martin oxidation / 5: Pinnick oxidation;
DOI:10.1039/c1cc12332g

Reference yield:

: 1314756-91-6
(E)-(2S,10R)-2-benzyloxy-1-{(4R,6S)-6-(2-hydroxyethyl)-2,2-dimethyl[1,3]dioxan-4-yl}-11-(4-methoxy-benzyloxy)-3,3-dimethyl-10-triethylsilyloxy-8-[(Z)-2-tri-isopropylsilyloxyethylidene]undec-5-en-4-one

: 1314757-00-0
prop-2-enyl (3R,5S,7S,9S,11S,15R)-7-benzyloxy-3-tert-butyldimethylsilyloxy-5,9-epoxy-11,15-epoxy-16-hydroxy-13-[(Z)-2-triisopropylsilyloxyethylidene]-9-methoxy-8,8-dimethylhexadecanoate

Guidance literature:: Multi-step reaction with 8 steps

1: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 0.42 h / 0 °C

2: potassium tert-butylate / tetrahydrofuran / 0.08 h / 20 °C

3: pyridine; Dess-Martin periodane / dichloromethane / 1 h / 20 °C

4: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene; water / tetrahydrofuran; tert-butyl alcohol / 1 h / 20 °C

5: sodium hydrogencarbonate / N,N-dimethyl-formamide / 16 h / 70 °C

6: pyridinium p-toluenesulfonate / methanol; dichloromethane / 1 h / 20 °C

7: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 °C

8: 2,3-dicyano-5,6-dichloro-p-benzoquinone / methanol; dichloromethane / 2 h / 20 °C

With pyridine; 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; potassium tert-butylate; water; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; pyridine hydrogenfluoride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 3: Dess-Martin oxidation / 4: Pinnick oxidation;
DOI:10.1039/c1cc12332g