methyl (2R,3aR,5S,6S,7S,7aS)-2-[(1S,2R)-2-(benzoyloxy)-1-hydroxybut-3-en-1-yl]-6,7-bis(benzyloxy)-7a-hydroxy-hexahydro-2H-furo[3,2-b]pyran-5-carboxylate

Base Information

Chemical Name:methyl (2R,3aR,5S,6S,7S,7aS)-2-[(1S,2R)-2-(benzoyloxy)-1-hydroxybut-3-en-1-yl]-6,7-bis(benzyloxy)-7a-hydroxy-hexahydro-2H-furo[3,2-b]pyran-5-carboxylate
CAS No.:1391973-99-1
Molecular Formula:C₃₄H₃₆O₁₀
Molecular Weight:604.654
Hs Code.:

methyl (2R,3aR,5S,6S,7S,7aS)-2-[(1S,2R)-2-(benzoyloxy)-1-hydroxybut-3-en-1-yl]-6,7-bis(benzyloxy)-7a-hydroxy-hexahydro-2H-furo[3,2-b]pyran-5-carboxylate

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Chemical Property of methyl (2R,3aR,5S,6S,7S,7aS)-2-[(1S,2R)-2-(benzoyloxy)-1-hydroxybut-3-en-1-yl]-6,7-bis(benzyloxy)-7a-hydroxy-hexahydro-2H-furo[3,2-b]pyran-5-carboxylate

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Technology Process of methyl (2R,3aR,5S,6S,7S,7aS)-2-[(1S,2R)-2-(benzoyloxy)-1-hydroxybut-3-en-1-yl]-6,7-bis(benzyloxy)-7a-hydroxy-hexahydro-2H-furo[3,2-b]pyran-5-carboxylate

There total 12 articles about methyl (2R,3aR,5S,6S,7S,7aS)-2-[(1S,2R)-2-(benzoyloxy)-1-hydroxybut-3-en-1-yl]-6,7-bis(benzyloxy)-7a-hydroxy-hexahydro-2H-furo[3,2-b]pyran-5-carboxylate 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:

: 1391973-98-0
methyl (2S,3S,4S,6R)-6-{[(4R,5S)-5-[(1R)-1-(benzoyloxy)prop-2-en-1-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-3,4-bis(benzyloxy)-5-oxooxane-2-carboxylate

: 1391973-99-1
methyl (2R,3aR,5S,6S,7S,7aS)-2-[(1S,2R)-2-(benzoyloxy)-1-hydroxybut-3-en-1-yl]-6,7-bis(benzyloxy)-7a-hydroxy-hexahydro-2H-furo[3,2-b]pyran-5-carboxylate

Guidance literature:: With trifluoroacetic acid; In dichloromethane; water; at 20 ℃; for 0.25h; Inert atmosphere;
DOI:10.1002/anie.201201826

Reference yield:

: 1391973-97-9
(1R)-1-[(4S,5R)-5-{[(2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-3-hydroxy-6-(hydroxymethyl)oxan-2-yl]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-yl benzoate

: 1391973-99-1
methyl (2R,3aR,5S,6S,7S,7aS)-2-[(1S,2R)-2-(benzoyloxy)-1-hydroxybut-3-en-1-yl]-6,7-bis(benzyloxy)-7a-hydroxy-hexahydro-2H-furo[3,2-b]pyran-5-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 4 h / 20 °C / Inert atmosphere

2: methanol; hexane; toluene / 1 h / 20 °C / Inert atmosphere

3: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.67 h / 20 °C / Inert atmosphere

4: trifluoroacetic acid / dichloromethane; water / 0.25 h / 20 °C / Inert atmosphere

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; sodium hydrogencarbonate; Dess-Martin periodane; trifluoroacetic acid; In methanol; hexane; dichloromethane; water; toluene;
DOI:10.1002/anie.201201826

Reference yield:

: C₃₆H₄₀O₁₀

: 1391973-99-1
methyl (2R,3aR,5S,6S,7S,7aS)-2-[(1S,2R)-2-(benzoyloxy)-1-hydroxybut-3-en-1-yl]-6,7-bis(benzyloxy)-7a-hydroxy-hexahydro-2H-furo[3,2-b]pyran-5-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: methanol; hexane; toluene / 1 h / 20 °C / Inert atmosphere

2: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.67 h / 20 °C / Inert atmosphere

3: trifluoroacetic acid / dichloromethane; water / 0.25 h / 20 °C / Inert atmosphere

With sodium hydrogencarbonate; Dess-Martin periodane; trifluoroacetic acid; In methanol; hexane; dichloromethane; water; toluene;
DOI:10.1002/anie.201201826