2,3,4-tri-O-benzyl-N-butyl-6-O-[1-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin

Base Information

Chemical Name:2,3,4-tri-O-benzyl-N-butyl-6-O-[1-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin
CAS No.:929619-06-7
Molecular Formula:C₄₇H₆₅NO₅
Molecular Weight:724.037
Hs Code.:

Synonyms:2,3,4-tri-O-benzyl-N-butyl-6-O-[1-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin

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Chemical Property of 2,3,4-tri-O-benzyl-N-butyl-6-O-[1-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin

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Technology Process of 2,3,4-tri-O-benzyl-N-butyl-6-O-[1-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin

There total 14 articles about 2,3,4-tri-O-benzyl-N-butyl-6-O-[1-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin 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: 82.0%

: 929619-05-6
2,3,4-tri-O-benzyl-6-O-[1-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin

: 123-72-8
butyraldehyde

: 929619-06-7
2,3,4-tri-O-benzyl-N-butyl-6-O-[1-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin

Guidance literature:: With sodium cyanoborohydride; acetic acid; In ethanol; at 20 ℃; for 20h;
DOI:10.1021/jo061280p

Reference yield:

: 929619-00-1
5-(adamantan-1-yl-methoxy)-1-benzyloxy-pentane

: 929619-06-7
2,3,4-tri-O-benzyl-N-butyl-6-O-[1-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / H₂ / Pd/C / ethanol / 20 h / 20 °C / 3750.3 Torr

2: 94 percent / CBr₄; PPh₃ / acetonitrile / 2.25 h / Heating

3: 92 percent / NaH / dimethylformamide / 6 h / 0 - 20 °C

4: 81 percent / I₂ / H₂O; tetrahydrofuran / 0.5 h / 20 °C

5: 82 percent / AcOH; NaBH₃CN / ethanol / 20 h / 20 °C

With carbon tetrabromide; hydrogen; iodine; sodium hydride; sodium cyanoborohydride; acetic acid; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo061280p

Reference yield:

: 770-71-8
1-adamantanemethanol

: 929619-06-7
2,3,4-tri-O-benzyl-N-butyl-6-O-[1-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaH / dimethylformamide / 1.5 h / 20 °C

1.2: 92 percent / dimethylformamide / 1 h / 75 °C

2.1: 97 percent / H₂ / Pd/C / ethanol / 20 h / 20 °C / 3750.3 Torr

3.1: 94 percent / CBr₄; PPh₃ / acetonitrile / 2.25 h / Heating

4.1: 92 percent / NaH / dimethylformamide / 6 h / 0 - 20 °C

5.1: 81 percent / I₂ / H₂O; tetrahydrofuran / 0.5 h / 20 °C

6.1: 82 percent / AcOH; NaBH₃CN / ethanol / 20 h / 20 °C

With carbon tetrabromide; hydrogen; iodine; sodium hydride; sodium cyanoborohydride; acetic acid; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo061280p