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

Base Information

Chemical Name: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
CAS No.:397870-68-7
Molecular Formula:C₂₂H₃₀O₈
Molecular Weight:422.475
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 5 articles about 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 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: 98.0%

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

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

: 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

Guidance literature:: In toluene; at 100 ℃; for 17h;
DOI:10.1246/bcsj.75.1927

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 3 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

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

Reference yield:

: 397870-67-6
6-O-benzyl-1,2-O-isopropylidene-3-O-methoxymethyl-α-D-gluco-hexofuranose

: 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

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / (COCl)2; dimethylsulfoxide; triethylamine / CH₂Cl₂ / 1.25 h / -78 - 0 °C

2: 98 percent / toluene / 17 h / 100 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; toluene; 1: Swern oxidation;
DOI:10.1246/bcsj.75.1927