Geranylgeraniol monophosphate

Base Information

• Chemical Name: Geranylgeraniol monophosphate
• CAS No.: 68982-81-0
• Molecular Formula: C₂₀H₃₅O₄P
• Molecular Weight: 370.469
• Nikkaji Number: J849.862H
• Mol file: 68982-81-0.mol

Synonyms:geranylgeraniol monophosphate;GGMP

Chemical Property of Geranylgeraniol monophosphate

Chemical Property:

• Vapor Pressure: 2.05E-11mmHg at 25°C
• Boiling Point: 501.4°C at 760 mmHg
• Flash Point: 257°C
• PSA: 0.00000
• Density: 1.035g/cm³
• LogP: 0.00000
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 12
• Exact Mass: 370.22729659
• Heavy Atom Count: 25
• Complexity: 546

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=CCCC(=CCCC(=CCCC(=CCOP(=O)(O)O)C)C)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CC/C(=C/CC/C(=C/COP(=O)(O)O)/C)/C)/C)C

Technology Process of Geranylgeraniol monophosphate

There total 17 articles about Geranylgeraniol monophosphate 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: 87.0%

Geranylgeraniol (24034-73-9) → geranylgeranyl phosphate (68982-81-0)

Guidance literature:

With pyruvate kinase; phosphoenolpyruvic acid; undecaprenol kinase; ATP; 2-amino-2-hydroxymethyl-1,3-propanediol; magnesium chloride; at 37 ℃; for 24h; pH=8; Kinetics; Enzymatic reaction;

DOI:10.1002/anie.201402313

Reference yield: 56.0%

(2Z,6Z,10Z)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ol (1945-42-2) → (2Z,6Z,10Z)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl phosphate (68982-81-0)

Guidance literature:

With tetrabutylammonium dihydrogen phosphate; trichloroacetonitrile; In dichloromethane; at 20 ℃; for 0.166667h;

Reference yield:

Nerol (106-25-2) → (2Z,6Z,10Z)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl phosphate (68982-81-0)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C

2.1: N-Bromosuccinimide / tetrahydrofuran; water / 6 h / 0 °C

2.2: 16 h / 20 °C

3.1: periodic acid / water; 1,4-dioxane / 12 h / 0 °C

4.1: sodium tetrahydroborate; ethanol / 3 h / 0 °C

5.1: pyridine / 3 h / 20 °C / Inert atmosphere

6.1: sodium iodide / acetone / 16 h / Reflux

7.1: toluene / 20 h / Inert atmosphere; Reflux

8.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C

8.2: 16 h / 20 °C

9.1: toluene-4-sulfonic acid / isopropyl alcohol; diethyl ether / 72 h / 20 °C

10.1: lithium chloride; 2,4,6-trimethyl-pyridine; methanesulfonyl chloride / N,N-dimethyl-formamide / 2 h / -3 °C

11.1: n-butyllithium; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / tetrahydrofuran / 2 h / -78 °C

11.2: 5.5 h / -30 °C

12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 0 °C

13.1: lithium triethylborohydride; bis(diphenylphosphino)propanepalladium(II) dichloride / tetrahydrofuran / 2 h / 0 °C

14.1: tetrabutylammonium dihydrogen phosphate; trichloroacetonitrile / dichloromethane / 0.17 h / 20 °C

With pyridine; 1H-imidazole; 2,4,6-trimethyl-pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; bis(diphenylphosphino)propanepalladium(II) dichloride; ethanol; tetrabutyl ammonium fluoride; lithium triethylborohydride; toluene-4-sulfonic acid; methanesulfonyl chloride; tetrabutylammonium dihydrogen phosphate; periodic acid; trichloroacetonitrile; sodium iodide; lithium chloride; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetone; toluene;

upstream raw materials:

Geranylgeraniol

(Z)-1-[(tert-butyldiphenylsilyl)oxy]-3,7-dimethyl-2,6-octadiene

(Z)-1-(tert-butyldiphenylsilyloxy)-6,7-epoxy-3,7-dimethylocta-2-ene

(Z)-1-[(tert-butyldiphenylsilyl)oxy]-3-methyl-2-hexen-6-al

Refernces

• 1、 Huang, Lin-Ya,Huang, Shih-Hsien,Chang, Ya-Chih,Cheng, Wei-Chieh,Cheng, Ting-Jen R.,Wong, Chi-Huey. "Enzymatic synthesis of lipid II and analogues". supporting information. p. 8060 - 8065. Retrieved 2014/08/18.