(4S,5S,8S,10S,E)-4,5,8-trihydroxy-10-methyl-4,5,9,10-tetrahydro-3H-oxecin-2(8H)-one

Base Information

Chemical Name:(4S,5S,8S,10S,E)-4,5,8-trihydroxy-10-methyl-4,5,9,10-tetrahydro-3H-oxecin-2(8H)-one
CAS No.:1566591-45-4
Molecular Formula:C₁₀H₁₆O₅
Molecular Weight:216.234
Hs Code.:

Synonyms:

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Chemical Property of (4S,5S,8S,10S,E)-4,5,8-trihydroxy-10-methyl-4,5,9,10-tetrahydro-3H-oxecin-2(8H)-one

Chemical Property:

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Technology Process of (4S,5S,8S,10S,E)-4,5,8-trihydroxy-10-methyl-4,5,9,10-tetrahydro-3H-oxecin-2(8H)-one

There total 11 articles about (4S,5S,8S,10S,E)-4,5,8-trihydroxy-10-methyl-4,5,9,10-tetrahydro-3H-oxecin-2(8H)-one 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: 61.0%

: 1566591-44-3
(3aS,7S,9S,11aS,E)-9-(methoxymethoxy)-2,2,7-trimethyl-3a,4,8,9-tetrahydro-7H-[1,3]dioxolo[4,5-d]oxecin-5(11aH)-one

: 1566591-45-4,147705-04-2
(4S,5S,8S,10S,E)-4,5,8-trihydroxy-10-methyl-4,5,9,10-tetrahydro-3H-oxecin-2(8H)-one

Guidance literature:: With boron trifluoride diethyl etherate; at 0 ℃; for 0.5h;
DOI:10.1016/j.tetasy.2013.12.008

Reference yield:

: C₁₆H₂₂O₄

: 1566591-45-4,147705-04-2
(4S,5S,8S,10S,E)-4,5,8-trihydroxy-10-methyl-4,5,9,10-tetrahydro-3H-oxecin-2(8H)-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: mercury(II) diacetate / tetrahydrofuran / 0.5 h / 0 - 20 °C

1.2: 1.5 h / 0 - 20 °C

2.1: 1H-imidazole / dichloromethane / 0.33 h / 20 °C

2.2: 2 h / 0 - 20 °C

3.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 12 h

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.25 h / -78 °C

4.2: -78 - 20 °C

5.1: potassium tert-butylate / tetrahydrofuran / 12 h / 0 - 20 °C

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2.17 h / 0 - 20 °C

7.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 6.08 h / 0 - 20 °C

8.1: 2-methyl-but-2-ene; sodium dihydrogenphosphate; sodium chlorite / tert-butyl alcohol; water; acetone / 12 h / 0 - 20 °C

9.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 12 h / 20 °C

10.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 24 h / Reflux

11.1: boron trifluoride diethyl etherate / 0.5 h / 0 °C

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; palladium 10% on activated carbon; boron trifluoride diethyl etherate; potassium tert-butylate; mercury(II) diacetate; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; dicyclohexyl-carbodiimide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; water; acetone; tert-butyl alcohol; 4.1: |Swern Oxidation / 4.2: |Swern Oxidation / 5.1: |Wittig Olefination;
DOI:10.1016/j.tetasy.2013.12.008

Reference yield:

: 562823-71-6
2-((4S,5S)-5-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol

: 1566591-45-4,147705-04-2
(4S,5S,8S,10S,E)-4,5,8-trihydroxy-10-methyl-4,5,9,10-tetrahydro-3H-oxecin-2(8H)-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: 1H-imidazole / dichloromethane / 0.33 h / 20 °C

1.2: 2 h / 0 - 20 °C

2.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 12 h

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.25 h / -78 °C

3.2: -78 - 20 °C

4.1: potassium tert-butylate / tetrahydrofuran / 12 h / 0 - 20 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2.17 h / 0 - 20 °C

6.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 6.08 h / 0 - 20 °C

7.1: 2-methyl-but-2-ene; sodium dihydrogenphosphate; sodium chlorite / tert-butyl alcohol; water; acetone / 12 h / 0 - 20 °C

8.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 12 h / 20 °C

9.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 24 h / Reflux

10.1: boron trifluoride diethyl etherate / 0.5 h / 0 °C

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; palladium 10% on activated carbon; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; dicyclohexyl-carbodiimide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; water; acetone; tert-butyl alcohol; 3.1: |Swern Oxidation / 3.2: |Swern Oxidation / 4.1: |Wittig Olefination;
DOI:10.1016/j.tetasy.2013.12.008