(3E)-4-[(4R)-4-(β-D-glucopyranosyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]but-3-en-2-one

Base Information

Chemical Name:(3E)-4-[(4R)-4-(β-D-glucopyranosyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]but-3-en-2-one
CAS No.:488128-40-1
Molecular Formula:C₁₉H₃₀O₇
Molecular Weight:370.443
Hs Code.:

Synonyms:(3E)-4-[(4R)-4-(β-D-glucopyranosyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]but-3-en-2-one

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Chemical Property of (3E)-4-[(4R)-4-(β-D-glucopyranosyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]but-3-en-2-one

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Technology Process of (3E)-4-[(4R)-4-(β-D-glucopyranosyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]but-3-en-2-one

There total 4 articles about (3E)-4-[(4R)-4-(β-D-glucopyranosyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]but-3-en-2-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: 85.0%

: 260244-82-4
C₄₇H₄₆O₁₁

: 488128-40-1
(3E)-4-[(4R)-4-(β-D-glucopyranosyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]but-3-en-2-one

Guidance literature:: C₄₇H₄₆O₁₁; With sodium methylate; In methanol; at 20 ℃; for 0.666667h;

With Dowex 50W-X₈ (H+); In methanol; at 20 ℃; for 0.5h;
DOI:10.1039/b204011p

Reference yield:

: 83021-07-2
(S,E)-4-[4-(tert-butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl]but-3-en-2-one

: 488128-40-1
(3E)-4-[(4R)-4-(β-D-glucopyranosyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]but-3-en-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 100 percent / aq. HF

2.1: 27 percent / PhSeOTf; 4 Angstroem molecular sieves / 1,2-dichloro-ethane / 1 h / 0 °C

3.1: NaOMe / methanol / 0.67 h / 20 °C

3.2: 85 percent / Dowex 50W-X₈ (H+) / methanol / 0.5 h / 20 °C

With 4 A molecular sieve; hydrogen fluoride; sodium methylate; phenylselenyl triflate; In methanol; 1,2-dichloro-ethane;
DOI:10.1039/b204011p

Reference yield:

: 50281-38-4
(3R)-3-hydroxy-β-ionone

: 488128-40-1
(3E)-4-[(4R)-4-(β-D-glucopyranosyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]but-3-en-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 27 percent / PhSeOTf; 4 Angstroem molecular sieves / 1,2-dichloro-ethane / 1 h / 0 °C

2.1: NaOMe / methanol / 0.67 h / 20 °C

2.2: 85 percent / Dowex 50W-X₈ (H+) / methanol / 0.5 h / 20 °C

With 4 A molecular sieve; sodium methylate; phenylselenyl triflate; In methanol; 1,2-dichloro-ethane;
DOI:10.1039/b204011p