6,10-anhydro-7,8,9-tri-O-benzyl-2-tert-butoxycarbonylamino-2,3,4,5,11-pentadeoxy-1,2-N,O-isopropylidene-L-threo-D-ido-undec-4-(Z)-enitol

Base Information

Chemical Name:6,10-anhydro-7,8,9-tri-O-benzyl-2-tert-butoxycarbonylamino-2,3,4,5,11-pentadeoxy-1,2-N,O-isopropylidene-L-threo-D-ido-undec-4-(Z)-enitol
CAS No.:740817-05-4
Molecular Formula:C₄₀H₅₁NO₇
Molecular Weight:657.847
Hs Code.:

6,10-anhydro-7,8,9-tri-O-benzyl-2-tert-butoxycarbonylamino-2,3,4,5,11-pentadeoxy-1,2-N,O-isopropylidene-L-threo-D-ido-undec-4-(Z)-enitol

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Chemical Property of 6,10-anhydro-7,8,9-tri-O-benzyl-2-tert-butoxycarbonylamino-2,3,4,5,11-pentadeoxy-1,2-N,O-isopropylidene-L-threo-D-ido-undec-4-(Z)-enitol

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Technology Process of 6,10-anhydro-7,8,9-tri-O-benzyl-2-tert-butoxycarbonylamino-2,3,4,5,11-pentadeoxy-1,2-N,O-isopropylidene-L-threo-D-ido-undec-4-(Z)-enitol

There total 9 articles about 6,10-anhydro-7,8,9-tri-O-benzyl-2-tert-butoxycarbonylamino-2,3,4,5,11-pentadeoxy-1,2-N,O-isopropylidene-L-threo-D-ido-undec-4-(Z)-enitol 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:

: 162118-38-9
(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol

: 740817-05-4
6,10-anhydro-7,8,9-tri-O-benzyl-2-tert-butoxycarbonylamino-2,3,4,5,11-pentadeoxy-1,2-N,O-isopropylidene-L-threo-D-ido-undec-4-(Z)-enitol

Guidance literature:: Multi-step reaction with 9 steps

1.1: 97 percent / pyridinium chlorochromate

2.1: nBuLi / diethyl ether; hexane / 1 h / -78 - -75 °C

2.2: 93 percent / diethyl ether; hexane / 1.5 h / -75 - -65 °C

3.1: 93 percent / triethylamine / CH₂Cl₂ / 42 h / 20 °C

4.1: 93 percent / samarium(II) iodide; ethylene glycol / tetrahydrofuran / 0.17 h

5.1: methyl triflate / acetonitrile / 0.25 h / 20 °C

5.2: NaBH₄ / methanol / 0.17 h / 20 °C

5.3: AgNO₃; H₂O / acetonitrile / 0.17 h / 20 °C

6.1: 95 percent / NaBH₄ / diethyl ether; methanol / 0.17 h / 20 °C

7.1: 93 percent / triphenylphosphine; imidazole; iodine / toluene / 1 h / 80 °C

8.1: 97 percent / 2 h / 120 °C

9.1: n-butyllithium / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 0.5 h / 0 °C

9.2: 75 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 3.5 h / -20 - 0 °C

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; samarium diiodide; iodine; ethylene glycol; triethylamine; triphenylphosphine; pyridinium chlorochromate; methyl trifluoromethanesulfonate; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; toluene; acetonitrile; 9.2: Wittig reaction;
DOI:10.1021/jo049406a

Reference yield:

: 138061-56-0
2,6-anhydro-3,4,5-tri-O-benzyl-7-deoxy-L-glycero-D-gluco-heptitol

: 740817-05-4
6,10-anhydro-7,8,9-tri-O-benzyl-2-tert-butoxycarbonylamino-2,3,4,5,11-pentadeoxy-1,2-N,O-isopropylidene-L-threo-D-ido-undec-4-(Z)-enitol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 93 percent / triphenylphosphine; imidazole; iodine / toluene / 1 h / 80 °C

2.1: 97 percent / 2 h / 120 °C

3.1: n-butyllithium / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 0.5 h / 0 °C

3.2: 75 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 3.5 h / -20 - 0 °C

With 1H-imidazole; n-butyllithium; iodine; triphenylphosphine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; toluene; 3.2: Wittig reaction;
DOI:10.1021/jo049406a

Reference yield:

: 163040-86-6
2,6-anhydro-3,4,5-tri-O-benzyl-7-deoxy-aldehydo-L-glycero-D-gluco-heptose

: 740817-05-4
6,10-anhydro-7,8,9-tri-O-benzyl-2-tert-butoxycarbonylamino-2,3,4,5,11-pentadeoxy-1,2-N,O-isopropylidene-L-threo-D-ido-undec-4-(Z)-enitol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 95 percent / NaBH₄ / diethyl ether; methanol / 0.17 h / 20 °C

2.1: 93 percent / triphenylphosphine; imidazole; iodine / toluene / 1 h / 80 °C

3.1: 97 percent / 2 h / 120 °C

4.1: n-butyllithium / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 0.5 h / 0 °C

4.2: 75 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 3.5 h / -20 - 0 °C

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; iodine; triphenylphosphine; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; toluene; 4.2: Wittig reaction;
DOI:10.1021/jo049406a