(E)-4-benzyloxy-3-{(1R,5R,7R,8S)-8-methoxymethoxy-3,3-dimethyl-2,4,6-trioxabicyclo[3.3.0]oct-7-yl}but-2-en-1-ol

Base Information

Chemical Name:(E)-4-benzyloxy-3-{(1R,5R,7R,8S)-8-methoxymethoxy-3,3-dimethyl-2,4,6-trioxabicyclo[3.3.0]oct-7-yl}but-2-en-1-ol
CAS No.:397870-78-9
Molecular Formula:C₂₀H₂₈O₇
Molecular Weight:380.438
Hs Code.:

Synonyms:(E)-4-benzyloxy-3-{(1R,5R,7R,8S)-8-methoxymethoxy-3,3-dimethyl-2,4,6-trioxabicyclo[3.3.0]oct-7-yl}but-2-en-1-ol

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Chemical Property of (E)-4-benzyloxy-3-{(1R,5R,7R,8S)-8-methoxymethoxy-3,3-dimethyl-2,4,6-trioxabicyclo[3.3.0]oct-7-yl}but-2-en-1-ol

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Technology Process of (E)-4-benzyloxy-3-{(1R,5R,7R,8S)-8-methoxymethoxy-3,3-dimethyl-2,4,6-trioxabicyclo[3.3.0]oct-7-yl}but-2-en-1-ol

There total 6 articles about (E)-4-benzyloxy-3-{(1R,5R,7R,8S)-8-methoxymethoxy-3,3-dimethyl-2,4,6-trioxabicyclo[3.3.0]oct-7-yl}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: 73.0%

: 397870-68-7
4-benzyloxy-3-{(1R,5R,7R,8S)-8-methoxymethoxy-3,3-dimethyl-2,4,6-trioxabicyclo[3.3.0]octan-7-yl}but-2-enoate

: 397870-69-8
(Z)-4-benzyloxy-3-{(1R,5R,7R,8S)-8-methoxymethoxy-3,3-dimethyl-2,4,6-trioxabicyclo[3.3.0]oct-7-yl}but-2-en-1-ol

: 397870-78-9
(E)-4-benzyloxy-3-{(1R,5R,7R,8S)-8-methoxymethoxy-3,3-dimethyl-2,4,6-trioxabicyclo[3.3.0]oct-7-yl}but-2-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -78 ℃; for 3h;
DOI:10.1246/bcsj.75.1927

Reference yield:

: 104487-62-9
1,2-O-isopropylidene-3-O-methoxymethyl-α-D-glucofuranose

: 397870-78-9
(E)-4-benzyloxy-3-{(1R,5R,7R,8S)-8-methoxymethoxy-3,3-dimethyl-2,4,6-trioxabicyclo[3.3.0]oct-7-yl}but-2-en-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: dibutyltin oxide / toluene / 3 h / Heating

1.2: 88 percent / CsF / dimethylformamide / 13 h / 80 °C

2.1: 100 percent / (COCl)2; dimethylsulfoxide; triethylamine / CH₂Cl₂ / 1.25 h / -78 - 0 °C

3.1: 98 percent / toluene / 17 h / 100 °C

4.1: 18 percent / DIBAL-H / toluene / 3 h / -78 °C

With oxalyl dichloride; diisobutylaluminium hydride; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; In dichloromethane; toluene; 2.1: Swern oxidation;
DOI:10.1246/bcsj.75.1927

Reference yield:

: 475291-30-6
6-O-benzyl-1,2-O-isopropylidene-3-O-methoxymethyl-α-D-xylo-hexofuranos-5-ulose

: 397870-78-9
(E)-4-benzyloxy-3-{(1R,5R,7R,8S)-8-methoxymethoxy-3,3-dimethyl-2,4,6-trioxabicyclo[3.3.0]oct-7-yl}but-2-en-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 98 percent / toluene / 17 h / 100 °C

2: 18 percent / DIBAL-H / toluene / 3 h / -78 °C

With diisobutylaluminium hydride; In toluene;
DOI:10.1246/bcsj.75.1927