5-(adamantan-1-yl-methoxy)pentyl 3,4,6-tri-O-benzyl-2,5-dideoxy-2,5-(pent-4-enimido)-D-talohexonamide

Base Information

Chemical Name:5-(adamantan-1-yl-methoxy)pentyl 3,4,6-tri-O-benzyl-2,5-dideoxy-2,5-(pent-4-enimido)-D-talohexonamide
CAS No.:1426549-67-8
Molecular Formula:C₄₈H₆₂N₂O₆
Molecular Weight:763.03
Hs Code.:

Synonyms:5-(adamantan-1-yl-methoxy)pentyl 3,4,6-tri-O-benzyl-2,5-dideoxy-2,5-(pent-4-enimido)-D-talohexonamide

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Chemical Property of 5-(adamantan-1-yl-methoxy)pentyl 3,4,6-tri-O-benzyl-2,5-dideoxy-2,5-(pent-4-enimido)-D-talohexonamide

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Technology Process of 5-(adamantan-1-yl-methoxy)pentyl 3,4,6-tri-O-benzyl-2,5-dideoxy-2,5-(pent-4-enimido)-D-talohexonamide

There total 6 articles about 5-(adamantan-1-yl-methoxy)pentyl 3,4,6-tri-O-benzyl-2,5-dideoxy-2,5-(pent-4-enimido)-D-talohexonamide 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:

: 591-80-0
pent-4-enoic acid

: 909870-16-2
(3R,4S,5R)-3,4-di-O-benzyl-5-(benzyloxymethyl)-1-pyrroline

: 1426549-65-6
N-[5-(adamantan-1-yl-methoxy)pentyl] Isocyanide

: 1426549-66-7
5-(adamantan-1-yl-methoxy)pentyl 3,4,6-tri-O-benzyl-2,5-dideoxy-2,5-(pent-4-enimido)-D-galactohexonamide

: 1426549-67-8
5-(adamantan-1-yl-methoxy)pentyl 3,4,6-tri-O-benzyl-2,5-dideoxy-2,5-(pent-4-enimido)-D-talohexonamide

Guidance literature:: With indium(III) chloride; In acetonitrile; at 0 - 5 ℃; for 20h; Overall yield = 47 %; Inert atmosphere;
DOI:10.1002/ejoc.201200923

Reference yield:

: 909870-15-1
2,3,5-tri-O-benzyl-4-deoxy-4-azido-D-lyxose

: 1426549-67-8
5-(adamantan-1-yl-methoxy)pentyl 3,4,6-tri-O-benzyl-2,5-dideoxy-2,5-(pent-4-enimido)-D-talohexonamide

Guidance literature:: Multi-step reaction with 2 steps

1: trimethylphosphane / methanol; toluene / 3 h / 0 °C / Inert atmosphere

2: indium(III) chloride / acetonitrile / 20 h / 0 - 5 °C / Inert atmosphere

With indium(III) chloride; trimethylphosphane; In methanol; toluene; acetonitrile; 2: |Ugi Condensation;
DOI:10.1002/ejoc.201200923

Reference yield:

: 850888-01-6
5-(adamantan-1-yl-methoxy)-1-bromo-pentane

: 1426549-67-8
5-(adamantan-1-yl-methoxy)pentyl 3,4,6-tri-O-benzyl-2,5-dideoxy-2,5-(pent-4-enimido)-D-talohexonamide

Guidance literature:: Multi-step reaction with 5 steps

1: sodium azide / dimethyl sulfoxide / 20 h / 20 °C / Inert atmosphere

2: water; trimethylphosphane / tetrahydrofuran / 3 h / 0 °C

3: dichloromethane / 20 h / 0 - 20 °C

4: triethylamine; trichlorophosphate / dichloromethane / 1 h / -30 °C / Inert atmosphere

5: indium(III) chloride / acetonitrile / 20 h / 0 - 5 °C / Inert atmosphere

With indium(III) chloride; sodium azide; water; triethylamine; trichlorophosphate; trimethylphosphane; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; acetonitrile; 5: |Ugi Condensation;
DOI:10.1002/ejoc.201200923