2,6-anhydro-3-azido-4-O-[(R)-3-(benzyloxy)tetradecyl]-3-deoxy-5,7-O-isopropylidene-D-glycero-D-ido-heptononitrile

Base Information

Chemical Name:2,6-anhydro-3-azido-4-O-[(R)-3-(benzyloxy)tetradecyl]-3-deoxy-5,7-O-isopropylidene-D-glycero-D-ido-heptononitrile
CAS No.:288402-92-6
Molecular Formula:C₃₁H₄₈N₄O₅
Molecular Weight:556.746
Hs Code.:

Synonyms:2,6-anhydro-3-azido-4-O-[(R)-3-(benzyloxy)tetradecyl]-3-deoxy-5,7-O-isopropylidene-D-glycero-D-ido-heptononitrile

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Chemical Property of 2,6-anhydro-3-azido-4-O-[(R)-3-(benzyloxy)tetradecyl]-3-deoxy-5,7-O-isopropylidene-D-glycero-D-ido-heptononitrile

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Technology Process of 2,6-anhydro-3-azido-4-O-[(R)-3-(benzyloxy)tetradecyl]-3-deoxy-5,7-O-isopropylidene-D-glycero-D-ido-heptononitrile

There total 10 articles about 2,6-anhydro-3-azido-4-O-[(R)-3-(benzyloxy)tetradecyl]-3-deoxy-5,7-O-isopropylidene-D-glycero-D-ido-heptononitrile 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%

: 288402-92-6
2,6-anhydro-3-azido-4-O-[(R)-3-(benzyloxy)tetradecyl]-3-deoxy-5,7-O-isopropylidene-D-glycero-D-ido-heptononitrile

Guidance literature:

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 288402-92-6
2,6-anhydro-3-azido-4-O-[(R)-3-(benzyloxy)tetradecyl]-3-deoxy-5,7-O-isopropylidene-D-glycero-D-ido-heptononitrile

Guidance literature:: Multi-step reaction with 7 steps

1.1: 97 percent / pTsOH*H₂O / dimethylformamide / 1 h / 20 °C

2.1: 95 percent / DIBAL / CH₂Cl₂ / 2 h / 0 °C

3.1: 96 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

4.1: 74 percent / NaH / dimethylformamide / 20 h / 20 °C

5.1: [C₈H₁₂Ir(PMePh₂)2]PF₆; H₂ / tetrahydrofuran / 3 h / 20 °C

5.2: 65 percent / I₂; water; pyridine / 12 h / 20 °C

6.1: 88 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

7.1: 93 percent / 4A MS / CH₂Cl₂ / 1 h / 20 °C

With [C₈H₁₂Ir(PMePh₂)2]PF₆; hydrogen; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(01)00055-6

Reference yield:

: 139623-13-5
(R)-1,3-dihydroxytetradecane

: 288402-92-6
2,6-anhydro-3-azido-4-O-[(R)-3-(benzyloxy)tetradecyl]-3-deoxy-5,7-O-isopropylidene-D-glycero-D-ido-heptononitrile

Guidance literature:: Multi-step reaction with 7 steps

1.1: 97 percent / pTsOH*H₂O / dimethylformamide / 1 h / 20 °C

2.1: 95 percent / DIBAL / CH₂Cl₂ / 2 h / 0 °C

3.1: 96 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

4.1: 74 percent / NaH / dimethylformamide / 20 h / 20 °C

5.1: [C₈H₁₂Ir(PMePh₂)2]PF₆; H₂ / tetrahydrofuran / 3 h / 20 °C

5.2: 65 percent / I₂; water; pyridine / 12 h / 20 °C

6.1: 88 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

7.1: 93 percent / 4A MS / CH₂Cl₂ / 1 h / 20 °C

With [C₈H₁₂Ir(PMePh₂)2]PF₆; hydrogen; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(01)00055-6