Gelsemiol

Base Information

• Chemical Name: Gelsemiol
• CAS No.: 110414-77-2
• Molecular Formula: C₁₀H₁₆O₄
• Molecular Weight: 200.235
• Mol file: 110414-77-2.mol

Synonyms:2H-Cyclopenta[b]furan-2-one,hexahydro-3,4-bis(hydroxymethyl)-5-methyl-, [3R-(3a,3aa,4b,5a,6aa)]-; Gelsemiol

Chemical Property of Gelsemiol

Chemical Property:

• Boiling Point: 407.0±10.0 °C(Predicted)
• PKA: 14.34±0.10(Predicted)
• PSA: 66.76000
• Density: 1.194±0.06 g/cm3(Predicted)
• LogP: -0.21520

Purity/Quality:

98%min ^*data from raw suppliers

Gelsemiol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Gelsemiol

There total 5 articles about Gelsemiol 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:

C18H24O6 → gelsemiol (110414-77-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydroxide / water / 24 h / 20 °C / Inert atmosphere

1.2: pH 8 - 9 / Inert atmosphere

2.1: iodine / tetrahydrofuran / 0.83 h / 0 °C / Inert atmosphere

3.1: dimethyl sulfide borane / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere

4.1: hydrogen / ethanol / 24 h / Inert atmosphere

With hydrogen; iodine; dimethyl sulfide borane; sodium hydroxide; In tetrahydrofuran; ethanol; water;

DOI:10.1002/chem.201203746

Reference yield:

C17H22O5 → gelsemiol (110414-77-2)

Guidance literature:

Multi-step reaction with 3 steps

1: iodine / tetrahydrofuran / 0.83 h / 0 °C / Inert atmosphere

2: dimethyl sulfide borane / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere

3: hydrogen / ethanol / 24 h / Inert atmosphere

With hydrogen; iodine; dimethyl sulfide borane; In tetrahydrofuran; ethanol;

DOI:10.1002/chem.201203746

Reference yield:

(3aS,4R,6aS)-methyl 4-((benzyloxy)methyl)-2-oxo-3,3a,4,6a-tetrahydro-2Hcyclopenta[b]furan-3-carboxylate → gelsemiol (110414-77-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: copper(I) bromide dimethyl sulphide complex / tetrahydrofuran; diethyl ether / 0.25 h / -18 °C / Inert atmosphere

1.2: 3.5 h / -48 - 48 °C / Inert atmosphere

2.1: sodium hydroxide / water / 24 h / 20 °C / Inert atmosphere

2.2: pH 8 - 9 / Inert atmosphere

3.1: iodine / tetrahydrofuran / 0.83 h / 0 °C / Inert atmosphere

4.1: dimethyl sulfide borane / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere

5.1: hydrogen / ethanol / 24 h / Inert atmosphere

With copper(I) bromide dimethyl sulphide complex; hydrogen; iodine; dimethyl sulfide borane; sodium hydroxide; In tetrahydrofuran; diethyl ether; ethanol; water;

DOI:10.1002/chem.201203746

upstream raw materials:

(3R,3aS,4S,5R,6R,6aR)-4-((benzyloxy)methyl)-6-iodo-5-methyl-2-oxohexahydro-2H-cyclopenta[b]furan-3-carboxylic acid

Refernces