(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

Base Information

• Chemical Name: (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
• CAS No.: 1391974-01-8
• Molecular Formula: C₃₆H₄₂O₉
• Molecular Weight: 618.724
• Mol file: 1391974-01-8.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 8 articles about (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 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: 77.0%

(1S)-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-yl benzoate (1391974-13-2) → (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)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1002/anie.201201826

Reference yield:

(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 (1391973-96-8) → (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)

Guidance literature:

Multi-step reaction with 2 steps

1: dmap; triethylamine / dichloromethane / 10 h / 0 - 20 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

With dmap; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1002/anie.201201826

Reference yield:

benzoyl chloride (98-88-4) → (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)

Guidance literature:

Multi-step reaction with 2 steps

1: dmap; triethylamine / dichloromethane / 10 h / 0 - 20 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

With dmap; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane;

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 (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

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

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