(3aR,4R,7S,8S,8aR)-benzyl 4-(benzyloxymethyl)-7,8-dihydroxy-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]azepine-5(4H)-carboxylate

Base Information

Chemical Name:(3aR,4R,7S,8S,8aR)-benzyl 4-(benzyloxymethyl)-7,8-dihydroxy-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]azepine-5(4H)-carboxylate
CAS No.:1384579-05-8
Molecular Formula:C₂₅H₃₁NO₇
Molecular Weight:457.524
Hs Code.:

Synonyms:(3aR,4R,7S,8S,8aR)-benzyl 4-(benzyloxymethyl)-7,8-dihydroxy-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]azepine-5(4H)-carboxylate

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Chemical Property of (3aR,4R,7S,8S,8aR)-benzyl 4-(benzyloxymethyl)-7,8-dihydroxy-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]azepine-5(4H)-carboxylate

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Technology Process of (3aR,4R,7S,8S,8aR)-benzyl 4-(benzyloxymethyl)-7,8-dihydroxy-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]azepine-5(4H)-carboxylate

There total 5 articles about (3aR,4R,7S,8S,8aR)-benzyl 4-(benzyloxymethyl)-7,8-dihydroxy-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]azepine-5(4H)-carboxylate 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: 64.0%

: 1384579-02-5
(3aR,4R,8aR)-benzyl 4-(benzyloxymethyl)-2,2-dimethyl-6,8a-dihydro-3aH-[1,3]dioxolo[4,5-c]azepine-5(4H)-carboxylate

: 1384579-06-9
(3aR,4R,7R,8R,8aR)-benzyl 4-(benzyloxymethyl)-7,8-dihydroxy-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]azepine-5(4H)-carboxylate

: 1384579-05-8
(3aR,4R,7S,8S,8aR)-benzyl 4-(benzyloxymethyl)-7,8-dihydroxy-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]azepine-5(4H)-carboxylate

Guidance literature:: With osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; In acetone; toluene; at 20 ℃; for 8h; optical yield given as %de;
DOI:10.1016/j.tetasy.2012.04.017

Reference yield:

: 1214915-00-0
benzyl (R)-2-(benzyloxy)-1-((4S,4'R,5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl) ethylcarbamate

: 1384579-06-9
(3aR,4R,7R,8R,8aR)-benzyl 4-(benzyloxymethyl)-7,8-dihydroxy-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]azepine-5(4H)-carboxylate

: 1384579-05-8
(3aR,4R,7S,8S,8aR)-benzyl 4-(benzyloxymethyl)-7,8-dihydroxy-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]azepine-5(4H)-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: dmap; sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C

2.1: water; acetic acid / 16 h / 20 °C

2.2: 0 °C / pH 7

3.1: 1H-imidazole; iodine; triphenylphosphine / toluene / 3 h / Reflux

4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 4 h / Reflux

5.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone; toluene / 8 h / 20 °C

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; osmium(VIII) oxide; water; iodine; sodium hydride; acetic acid; 4-methylmorpholine N-oxide; triphenylphosphine; In dichloromethane; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1016/j.tetasy.2012.04.017

Reference yield:

: 1384579-00-3
benzyl allyl((R)-2-(benzyloxy)-1-((4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)ethyl)carbamate

: 1384579-06-9
(3aR,4R,7R,8R,8aR)-benzyl 4-(benzyloxymethyl)-7,8-dihydroxy-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]azepine-5(4H)-carboxylate

: 1384579-05-8
(3aR,4R,7S,8S,8aR)-benzyl 4-(benzyloxymethyl)-7,8-dihydroxy-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]azepine-5(4H)-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 4 h / Reflux

2: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone; toluene / 8 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; In dichloromethane; acetone; toluene;
DOI:10.1016/j.tetasy.2012.04.017