(+)-abscisyl alcohol

Base Information

• Chemical Name: (+)-abscisyl alcohol
• CAS No.: 56298-25-0
• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.338
• Mol file: 56298-25-0.mol

Synonyms:(+)-abscisyl alcohol

Chemical Property of (+)-abscisyl alcohol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-abscisyl alcohol

There total 6 articles about (+)-abscisyl alcohol 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%

(2Z,4E)-5-<(S)-1-Hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl>-3-methylpenta-2,4-dienal (41944-86-9) → methyl (1'S,2Z,4E,4'S)-5-(1,4-dihydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-ol (69350-40-9) + (+)-abscisyl alcohol (56298-25-0) + (1S,4R)-1-((1E,3Z)-5-Hydroxy-3-methyl-penta-1,3-dienyl)-2,6,6-trimethyl-cyclohex-2-ene-1,4-diol

Guidance literature:

With sodium tetrahydroborate; In methanol; dichloromethane; at -78 ℃; for 3h; Yields of byproduct given;

DOI:10.1080/00397919708006821

Reference yield: 55.0%

(+)-8(2Z,4E)-(2S,3S,8R)-8-(5-hydroxy-3-methyl-2,4-pentadienyl)-2,3,7,9,9-pentamethyl-1,4-dioxaspiro<4.5>dec-6-en-8-ol (141245-65-0) → (+)-abscisyl alcohol (56298-25-0)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; for 6h; Ambient temperature;

DOI:10.1016/S0957-4166(00)80288-8

Reference yield:

(Z)-tert-butyldimethyl((3-methylpent-2-en-4-yn-1-yl)oxy)silane (117431-83-1,121693-79-6) → (+)-abscisyl alcohol (56298-25-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) n-butyllithium / 1.) THF, hexane, from -40 deg C to -78 deg C, 70 min, 2.) THF, hexane, from -78 deg C to -10 deg C, 30 min

2: 65 percent / sodium bis(2-methoxyethoxy) aluminium hydride (Redal) / tetrahydrofuran; toluene / 2 h / Ambient temperature

3: 55 percent / p-toluenesulfonic acid monohydrate / acetone / 6 h / Ambient temperature

With n-butyllithium; toluene-4-sulfonic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; acetone; toluene;

DOI:10.1016/S0957-4166(00)80288-8

upstream raw materials:

(+)-8(2Z,4E)-(2S,3S,8R)-8-(5-hydroxy-3-methyl-2,4-pentadienyl)-2,3,7,9,9-pentamethyl-1,4-dioxaspiro<4.5>dec-6-en-8-ol

Abscisic acid

(2Z,4E)-5-<(S)-1-Hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl>-3-methylpenta-2,4-dienal

(Z)-tert-butyldimethyl((3-methylpent-2-en-4-yn-1-yl)oxy)silane

Downstream raw materials:

methyl (1'S,2Z,4E,4'S)-5-(1,4-dihydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-ol

(2Z,4E)-5-<(S)-1-Hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl>-3-methylpenta-2,4-dienal

Refernces

• 1、 Rose,Abrams,Shaw. "Synthesis of chiral acetylenic analogs of the plant hormone abscisic acid". . p. 443 - 450. Retrieved 2007/10/02.