(E)-3-[(2R,3R,5S)-3-benzyloxy-5-methoxyoxolan-2-yl]-4-(4-methoxybenzyloxy)but-2-en-1-ol

Base Information

Chemical Name:(E)-3-[(2R,3R,5S)-3-benzyloxy-5-methoxyoxolan-2-yl]-4-(4-methoxybenzyloxy)but-2-en-1-ol
CAS No.:184964-62-3
Molecular Formula:C₂₄H₃₀O₆
Molecular Weight:414.499
Hs Code.:

Synonyms:(E)-3-[(2R,3R,5S)-3-benzyloxy-5-methoxyoxolan-2-yl]-4-(4-methoxybenzyloxy)but-2-en-1-ol

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Chemical Property of (E)-3-[(2R,3R,5S)-3-benzyloxy-5-methoxyoxolan-2-yl]-4-(4-methoxybenzyloxy)but-2-en-1-ol

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Technology Process of (E)-3-[(2R,3R,5S)-3-benzyloxy-5-methoxyoxolan-2-yl]-4-(4-methoxybenzyloxy)but-2-en-1-ol

There total 11 articles about (E)-3-[(2R,3R,5S)-3-benzyloxy-5-methoxyoxolan-2-yl]-4-(4-methoxybenzyloxy)but-2-en-1-ol 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: 93.0%

: methyl 3-[(2R,3R,5S)-3-benzyloxy-5-methoxyoxolan-2-yl]-4-(4-methoxybenzyloxy)but-2-enoate

: 184964-65-6
(Z)-3-[(2R,3R,5S)-3-benzyloxy-5-methoxyoxolan-2-yl]-4-(4-methoxybenzyloxy)but-2-en-1-ol

: 184964-62-3
(E)-3-[(2R,3R,5S)-3-benzyloxy-5-methoxyoxolan-2-yl]-4-(4-methoxybenzyloxy)but-2-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at -78 ℃; for 0.25h;
DOI:10.1246/bcsj.75.1927

Reference yield:

: 79241-07-9
(R)-4-((2S,3R)-3-(benzyloxy)-2,3-dihydrofuran-2-yl)-2,2-dimethyl-1,3-dioxolan

: 184964-62-3
(E)-3-[(2R,3R,5S)-3-benzyloxy-5-methoxyoxolan-2-yl]-4-(4-methoxybenzyloxy)but-2-en-1-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: Hg(OAc)2; water / tetrahydrofuran / 0.5 h / 25 °C

1.2: potassium iodide / tetrahydrofuran; H₂O / 0.25 h / 0 °C

1.3: NaBH₄ / tetrahydrofuran; H₂O / 1.5 h / 0 °C

2.1: 91 percent / acetic acid; water / 14 h / 25 °C

3.1: 69 percent / AcCl / 20 h / 0 °C

4.1: dibutyltin oxide / toluene / 2 h / Heating

4.2: 96 percent / CsF / dimethylformamide / 40 h / 80 °C

5.1: 100 percent / (COCl)2; dimethylsulfoxide; triethylamine / CH₂Cl₂ / 3.5 h / -78 - 0 °C

6.1: 90 percent / LiBr; DBU / acetonitrile / 12 h / -45 °C

7.1: 93 percent / DIBAL-H; DBU / toluene / 0.25 h / -78 °C

With oxalyl dichloride; mercury(II) diacetate; water; diisobutylaluminium hydride; di(n-butyl)tin oxide; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; acetyl chloride; lithium bromide; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; 5.1: Swern oxidation;
DOI:10.1246/bcsj.75.1927

Reference yield:

: 386765-77-1
methyl 3-O-benzyl-6-O-(4-methoxybenzyl)-2-deoxy-α-D-threo-hexofuranos-5-uloside

: 184964-62-3
(E)-3-[(2R,3R,5S)-3-benzyloxy-5-methoxyoxolan-2-yl]-4-(4-methoxybenzyloxy)but-2-en-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / LiBr; DBU / acetonitrile / 12 h / -45 °C

2: 93 percent / DIBAL-H; DBU / toluene / 0.25 h / -78 °C

With diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium bromide; In toluene; acetonitrile;
DOI:10.1246/bcsj.75.1927