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

Base Information

• Chemical Name: methyl (2S,3S,4S,6R)-6-{[(4R,5S)-5-[(1S)-(benzoyloxy)prop-2-en-1-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-3,4-bis(benzyloxy)-5-oxooxane-2-carboxylate
• CAS No.: 1391973-86-6
• Molecular Formula: C₃₇H₄₀O₁₀
• Molecular Weight: 644.719
• Mol file: 1391973-86-6.mol

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

Chemical Property of methyl (2S,3S,4S,6R)-6-{[(4R,5S)-5-[(1S)-(benzoyloxy)prop-2-en-1-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-3,4-bis(benzyloxy)-5-oxooxane-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2S,3S,4S,6R)-6-{[(4R,5S)-5-[(1S)-(benzoyloxy)prop-2-en-1-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-3,4-bis(benzyloxy)-5-oxooxane-2-carboxylate

There total 11 articles about methyl (2S,3S,4S,6R)-6-{[(4R,5S)-5-[(1S)-(benzoyloxy)prop-2-en-1-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-3,4-bis(benzyloxy)-5-oxooxane-2-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: 94.0%

methyl (2S,3S,4R,5S,6R)-6-{[(4R,5S)-5-[(1S)-1-(benzoyloxy)prop-2-en-1-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-3,4-bis(benzyloxy)-5-hydroxyoxane-2-carboxylate (1391974-14-3) → methyl (2S,3S,4S,6R)-6-{[(4R,5S)-5-[(1S)-(benzoyloxy)prop-2-en-1-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-3,4-bis(benzyloxy)-5-oxooxane-2-carboxylate (1391973-86-6)

Guidance literature:

With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/anie.201201826

Reference yield:

(1S)-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 (1391974-01-8) → methyl (2S,3S,4S,6R)-6-{[(4R,5S)-5-[(1S)-(benzoyloxy)prop-2-en-1-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-3,4-bis(benzyloxy)-5-oxooxane-2-carboxylate (1391973-86-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 5.5 h / 20 °C / Inert atmosphere

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

3: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; sodium hydrogencarbonate; Dess-Martin periodane; In methanol; hexane; dichloromethane; toluene;

DOI:10.1002/anie.201201826

Reference yield:

C36H40O10 → methyl (2S,3S,4S,6R)-6-{[(4R,5S)-5-[(1S)-(benzoyloxy)prop-2-en-1-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-3,4-bis(benzyloxy)-5-oxooxane-2-carboxylate (1391973-86-6)

Guidance literature:

Multi-step reaction with 2 steps

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

2: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

With sodium hydrogencarbonate; Dess-Martin periodane; In methanol; hexane; dichloromethane; toluene;

DOI:10.1002/anie.201201826

upstream raw materials:

methyl (4S,5R)-5-{[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]methyl}-2,2-dimethyl-1,3-dioxolane-4-carboxylate

(4S,5R)-5-{[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]methyl}-N-methoxy-N,2,2-trimethyl-1,3-dioxolane-4-carboxamide

1-[(4S,5R)-5-{[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-one

(1S)-1-[(4R,5R)-5-{[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol

Downstream raw materials:

methyl (1R,3S,4R,5S,7R,9R,11S,12S,13S)-5-(acetyloxy)-4-(benzoyloxy)-12,13-bis(benzyloxy)-1-hydroxy-2,6,10-trioxatricyclo[7.4.0.0^3,7]tridecane-11-carboxylate

methyl (1R,3S,4R,5R,7R,9R,11S,12S,13S)-5-(acetyloxy)-4-(benzoyloxy)-12,13-bis(benzyloxy)-1-hydroxy-2,6,10-trioxatricyclo[7.4.0.0^3,7]tridecane-11-carboxylate

methyl (1S,3S,4R,7R,9R,11S,12S,13S)-5-(acetyloxy)-4-(benzoyloxy)-1,12,13-trihydroxy-2,6,10-trioxatricyclo[7.4.0.0(3,7)]tridecane-11-carboxylate

methyl (1R,3S,4R,5R,7R,9R,11S,12S,13S)-5,12,13-tris(acetyloxy)-4-(benzoyloxy)-1-hydroxy-2,6,10-trioxatricyclo[7.4.0.0^3,7]tridecane-11-carboxylate