(E)-methyl 2-((S)-2-((2R,3R)-2,3-bis(benzyloxy)butyl)tetrahydro-6-oxopyran-4-ylidene)acetate

Base Information

• Chemical Name: (E)-methyl 2-((S)-2-((2R,3R)-2,3-bis(benzyloxy)butyl)tetrahydro-6-oxopyran-4-ylidene)acetate
• CAS No.: 1619900-48-9
• Molecular Formula: C₂₆H₃₀O₆
• Molecular Weight: 438.521
• Mol file: 1619900-48-9.mol

Synonyms:

Chemical Property of (E)-methyl 2-((S)-2-((2R,3R)-2,3-bis(benzyloxy)butyl)tetrahydro-6-oxopyran-4-ylidene)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-methyl 2-((S)-2-((2R,3R)-2,3-bis(benzyloxy)butyl)tetrahydro-6-oxopyran-4-ylidene)acetate

There total 11 articles about (E)-methyl 2-((S)-2-((2R,3R)-2,3-bis(benzyloxy)butyl)tetrahydro-6-oxopyran-4-ylidene)acetate 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:

1-(((R)-1-(4-methoxybenzyloxy)propan-2-yloxy)methyl)benzene (1105507-44-5) → (E)-methyl 2-((S)-2-((2R,3R)-2,3-bis(benzyloxy)butyl)tetrahydro-6-oxopyran-4-ylidene)acetate (1619900-48-9)

Guidance literature:

Multi-step reaction with 12 steps

1.1: ammonium cerium (IV) nitrate / acetonitrile; water / 1 h / 0 - 20 °C

2.1: oxalyl dichloride; dimethylsulfone / dichloromethane / 2 h / -78 °C

2.2: 1 h / -78 °C

3.1: dichloromethane / 1 h / -78 - -40 °C / Inert atmosphere

4.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C

4.2: 16 h / 20 °C

5.1: (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane] / water; tert-butyl alcohol / 18 h / 0 °C

6.1: triethylamine / dichloromethane / 16 h / 0 - 20 °C

7.1: potassium carbonate / methanol / 1 h / 0 - 20 °C

8.1: boron trifluoride diethyl etherate; n-butyllithium / tetrahydrofuran / -78 °C / Inert atmosphere

8.2: 1 h / -78 °C / Inert atmosphere

9.1: N-Bromosuccinimide / dichloromethane / 16 h / 0 - 20 °C

10.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 2 h / Inert atmosphere; Reflux

11.1: acetic acid / water / 1 h / 55 - 60 °C / Reflux

12.1: Dess-Martin periodane / dichloromethane / 2 h / 0 °C / Inert atmosphere

With N-Bromosuccinimide; n-butyllithium; ammonium cerium (IV) nitrate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); dimethylsulfone; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; sodium hydride; potassium carbonate; Dess-Martin periodane; acetic acid; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane]; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol; 2.1: |Swern Oxidation / 2.2: |Swern Oxidation / 3.1: |Grignard Reaction / 5.1: |Sharpless Dihydroxylation;

DOI:10.1016/j.tetlet.2014.05.116

Reference yield:

(R)-2-benzyloxypropanal (53346-05-7,41954-96-5,81445-44-5,81445-45-6) → (E)-methyl 2-((S)-2-((2R,3R)-2,3-bis(benzyloxy)butyl)tetrahydro-6-oxopyran-4-ylidene)acetate (1619900-48-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: dichloromethane / 1 h / -78 - -40 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C

2.2: 16 h / 20 °C

3.1: (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane] / water; tert-butyl alcohol / 18 h / 0 °C

4.1: triethylamine / dichloromethane / 16 h / 0 - 20 °C

5.1: potassium carbonate / methanol / 1 h / 0 - 20 °C

6.1: boron trifluoride diethyl etherate; n-butyllithium / tetrahydrofuran / -78 °C / Inert atmosphere

6.2: 1 h / -78 °C / Inert atmosphere

7.1: N-Bromosuccinimide / dichloromethane / 16 h / 0 - 20 °C

8.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 2 h / Inert atmosphere; Reflux

9.1: acetic acid / water / 1 h / 55 - 60 °C / Reflux

10.1: Dess-Martin periodane / dichloromethane / 2 h / 0 °C / Inert atmosphere

With N-Bromosuccinimide; n-butyllithium; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; sodium hydride; potassium carbonate; Dess-Martin periodane; acetic acid; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane]; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; toluene; tert-butyl alcohol; 1.1: |Grignard Reaction / 3.1: |Sharpless Dihydroxylation;

DOI:10.1016/j.tetlet.2014.05.116

Reference yield:

(R)-2-(benzyloxy)propan-1-ol (87037-69-2) → (E)-methyl 2-((S)-2-((2R,3R)-2,3-bis(benzyloxy)butyl)tetrahydro-6-oxopyran-4-ylidene)acetate (1619900-48-9)

Guidance literature:

Multi-step reaction with 11 steps

1.1: oxalyl dichloride; dimethylsulfone / dichloromethane / 2 h / -78 °C

1.2: 1 h / -78 °C

2.1: dichloromethane / 1 h / -78 - -40 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C

3.2: 16 h / 20 °C

4.1: (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane] / water; tert-butyl alcohol / 18 h / 0 °C

5.1: triethylamine / dichloromethane / 16 h / 0 - 20 °C

6.1: potassium carbonate / methanol / 1 h / 0 - 20 °C

7.1: boron trifluoride diethyl etherate; n-butyllithium / tetrahydrofuran / -78 °C / Inert atmosphere

7.2: 1 h / -78 °C / Inert atmosphere

8.1: N-Bromosuccinimide / dichloromethane / 16 h / 0 - 20 °C

9.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 2 h / Inert atmosphere; Reflux

10.1: acetic acid / water / 1 h / 55 - 60 °C / Reflux

11.1: Dess-Martin periodane / dichloromethane / 2 h / 0 °C / Inert atmosphere

With N-Bromosuccinimide; n-butyllithium; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); dimethylsulfone; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; sodium hydride; potassium carbonate; Dess-Martin periodane; acetic acid; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane]; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; toluene; tert-butyl alcohol; 1.1: |Swern Oxidation / 1.2: |Swern Oxidation / 2.1: |Grignard Reaction / 4.1: |Sharpless Dihydroxylation;

DOI:10.1016/j.tetlet.2014.05.116

upstream raw materials:

(2R,4R,5R)-4,5-bis(benzyloxy)hexane-1,2-diol

(2R,4R,5R)-4,5-bis(benzyloxy)-2-hydroxyhexyl-4-methylbenzenesulfonate

(R)-2-((2R,3R)-2,3-bis(benzyloxy)butyl)oxirane

(5S,7R,8R)-methyl 7,8-bis(benzyloxy)-5-hydroxynon-2-ynoate