(all-E)-(3R)-3-(β-D-glucopyranosyloxy)-β,β-carotene

Base Information

• Chemical Name: (all-E)-(3R)-3-(β-D-glucopyranosyloxy)-β,β-carotene
• CAS No.: 135589-15-0
• Molecular Formula: C₄₆H₆₆O₆
• Molecular Weight: 715.026
• Mol file: 135589-15-0.mol

Synonyms:

Chemical Property of (all-E)-(3R)-3-(β-D-glucopyranosyloxy)-β,β-carotene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (all-E)-(3R)-3-(β-D-glucopyranosyloxy)-β,β-carotene

There total 15 articles about (all-E)-(3R)-3-(β-D-glucopyranosyloxy)-β,β-carotene 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: 28.0%

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) + 13-[(4R)-4-(β-D-glucopyranosyloxy)-2,6,6-trimethylcyclohex-1-enyl]-2,7,11-trimethyltrideca-2,4,6,8,10,12-hexaenal → (all-E)-(3R)-3-(β-D-glucopyranosyloxy)-β,β-carotene (135589-15-0) + (9'Z)-(3R)-3-(β-D-glucopyranosyloxy)-β,β-carotene

Guidance literature:

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide; 13-[(4R)-4-(β-D-glucopyranosyloxy)-2,6,6-trimethylcyclohex-1-enyl]-2,7,11-trimethyltrideca-2,4,6,8,10,12-hexaenal; With sodium methylate; In methanol; dichloromethane; at 20 ℃; for 3h;

With Dowex 50W-X₈ (H+); In methanol; dichloromethane; at 20 ℃; for 0.333333h;

DOI:10.1039/b204011p

Reference yield: 28.0%

[(2E,4E)-3-Methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dienyl]-triphenyl-phosphonium; bromide (49817-17-6) + 13-[(4R)-4-(β-D-glucopyranosyloxy)-2,6,6-trimethylcyclohex-1-enyl]-2,7,11-trimethyltrideca-2,4,6,8,10,12-hexaenal → (2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-{(R)-3,5,5-trimethyl-4-[(1E,3Z,5Z,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethyl-cyclohex-1-enyl)-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-cyclohex-3-enyloxy}-tetrahydro-pyran-3,4,5-triol + (all-E)-(3R)-3-(β-D-glucopyranosyloxy)-β,β-carotene (135589-15-0)

Guidance literature:

With sodium methylate;

DOI:10.3987/com-99-s54

Reference yield:

methyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside (104707-00-8) → (all-E)-(3R)-3-(β-D-glucopyranosyloxy)-β,β-carotene (135589-15-0)

Guidance literature:

Multi-step reaction with 4 steps

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

2.1: s-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

2.2: tetrahydrofuran; hexane / 0.33 h / -78 °C

2.3: aq. oxalic acid

3.1: NaOMe / methanol; CH₂Cl₂ / 1 h / 0 - 20 °C

3.2: Dowex 50W-X₈ (H+) / methanol; CH₂Cl₂ / 0.25 h / 20 °C

4.1: NaOMe / CH₂Cl₂; methanol / 3 h / 20 °C

4.2: 28 percent / Dowex 50W-X₈ (H+) / CH₂Cl₂; methanol / 0.33 h / 20 °C

With 4 A molecular sieve; sec.-butyllithium; sodium methylate; phenylselenyl triflate; In tetrahydrofuran; methanol; hexane; dichloromethane; 1,2-dichloro-ethane; 2.2: Peterson reaction / 4.1: Wittig condensation;

DOI:10.1039/b204011p

upstream raw materials:

[(2E,4E)-3-Methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dienyl]-triphenyl-phosphonium; bromide

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

methyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside

all-trans-(7-Formyl-2-methyl-2,4,6-octatrienyl)triphenylphosphoniumchlorid