3-[2-hydroxy-3-(4-methoxy-benzyloxy)-propyl]-6-(4-methoxy-benzyloxy)-hex-2-ene-1,5-diol

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Chemical Name:3-[2-hydroxy-3-(4-methoxy-benzyloxy)-propyl]-6-(4-methoxy-benzyloxy)-hex-2-ene-1,5-diol
CAS No.:290815-60-0
Molecular Formula:C₂₅H₃₄O₇
Molecular Weight:446.541
Hs Code.:

Synonyms:3-[2-hydroxy-3-(4-methoxy-benzyloxy)-propyl]-6-(4-methoxy-benzyloxy)-hex-2-ene-1,5-diol

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Chemical Property of 3-[2-hydroxy-3-(4-methoxy-benzyloxy)-propyl]-6-(4-methoxy-benzyloxy)-hex-2-ene-1,5-diol

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Technology Process of 3-[2-hydroxy-3-(4-methoxy-benzyloxy)-propyl]-6-(4-methoxy-benzyloxy)-hex-2-ene-1,5-diol

There total 7 articles about 3-[2-hydroxy-3-(4-methoxy-benzyloxy)-propyl]-6-(4-methoxy-benzyloxy)-hex-2-ene-1,5-diol 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: 90.0%

: 290815-59-7
5-(tert-butyl-dimethyl-silanyloxy)-3-[2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-6-(4-methoxy-benzyloxy)-hex-2-en-1-ol

: 290815-60-0
3-[2-hydroxy-3-(4-methoxy-benzyloxy)-propyl]-6-(4-methoxy-benzyloxy)-hex-2-ene-1,5-diol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 8h;
DOI:10.1021/ol005850y

Reference yield:

: 80910-01-6,108836-41-5,144069-33-0,134733-19-0
(R)-2-(((4-methoxybenzyl)oxy)methyl)oxirane

: 290815-60-0
3-[2-hydroxy-3-(4-methoxy-benzyloxy)-propyl]-6-(4-methoxy-benzyloxy)-hex-2-ene-1,5-diol

Guidance literature:: Multi-step reaction with 7 steps

1.1: n-BuLi; HMPA / tetrahydrofuran / 0.5 h / -78 °C

1.2: tetrahydrofuran / 1.5 h / -78 - 0 °C

1.3: 87 percent / tetrahydrofuran / -78 - 20 °C

2.1: 86 percent / Hg(ClO₄)*xH₂O; CaCO₃; H₂O / tetrahydrofuran / 0.3 h / 0 °C

3.1: 80 percent / tetrahydrofuran / 0.3 h / 0 °C

4.1: 76 percent / OsO₄; NaIO₄ / tetrahydrofuran; H₂O

5.1: 80 percent / TFAA; DMAP; Et₃N / CH₂Cl₂ / 16 h / 45 °C

6.1: 90 percent / i-Bu₂AlH / CH₂Cl₂ / 5 h / -78 °C

7.1: 90 percent / TBAF / tetrahydrofuran / 8 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium periodate; osmium(VIII) oxide; n-butyllithium; mercury(I) perchlorate; tetrabutyl ammonium fluoride; water; diisobutylaluminium hydride; triethylamine; trifluoroacetic anhydride; calcium carbonate; In tetrahydrofuran; dichloromethane; water; 1.1: Metallation / 1.2: Addition / 1.3: Condensation / 2.1: Hydrolysis / 3.1: Addition / 4.1: Oxidation / 5.1: Dehydration / 6.1: Reduction / 7.1: Substitution;
DOI:10.1021/ol005850y

Reference yield:

: 290815-54-2
(2R,6R)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-1,7-bis-(4-methoxy-benzyloxy)-heptan-4-one

: 290815-60-0
3-[2-hydroxy-3-(4-methoxy-benzyloxy)-propyl]-6-(4-methoxy-benzyloxy)-hex-2-ene-1,5-diol

Guidance literature:: Multi-step reaction with 5 steps

1: 80 percent / tetrahydrofuran / 0.3 h / 0 °C

2: 76 percent / OsO₄; NaIO₄ / tetrahydrofuran; H₂O

3: 80 percent / TFAA; DMAP; Et₃N / CH₂Cl₂ / 16 h / 45 °C

4: 90 percent / i-Bu₂AlH / CH₂Cl₂ / 5 h / -78 °C

5: 90 percent / TBAF / tetrahydrofuran / 8 h / 20 °C

With dmap; sodium periodate; osmium(VIII) oxide; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; water; 1: Addition / 2: Oxidation / 3: Dehydration / 4: Reduction / 5: Substitution;
DOI:10.1021/ol005850y