(3S,4aR,6R,7R,8S)-6,7-bis(benzyloxy)-8-(benzyloxymethyl)-3-(dec-2-en-1-yl)hexahydropyrido[1,2-c][1,3]oxazin-1(3H)-one

Base Information

Chemical Name:(3S,4aR,6R,7R,8S)-6,7-bis(benzyloxy)-8-(benzyloxymethyl)-3-(dec-2-en-1-yl)hexahydropyrido[1,2-c][1,3]oxazin-1(3H)-one
CAS No.:1454313-47-3
Molecular Formula:C₄₀H₅₁NO₅
Molecular Weight:625.849
Hs Code.:

Synonyms:(3S,4aR,6R,7R,8S)-6,7-bis(benzyloxy)-8-(benzyloxymethyl)-3-(dec-2-en-1-yl)hexahydropyrido[1,2-c][1,3]oxazin-1(3H)-one

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Chemical Property of (3S,4aR,6R,7R,8S)-6,7-bis(benzyloxy)-8-(benzyloxymethyl)-3-(dec-2-en-1-yl)hexahydropyrido[1,2-c][1,3]oxazin-1(3H)-one

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Technology Process of (3S,4aR,6R,7R,8S)-6,7-bis(benzyloxy)-8-(benzyloxymethyl)-3-(dec-2-en-1-yl)hexahydropyrido[1,2-c][1,3]oxazin-1(3H)-one

There total 11 articles about (3S,4aR,6R,7R,8S)-6,7-bis(benzyloxy)-8-(benzyloxymethyl)-3-(dec-2-en-1-yl)hexahydropyrido[1,2-c][1,3]oxazin-1(3H)-one 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: 90.0%

: 124-11-8
non-1-ene

: 1454313-46-2
(3S,4aR,6R,7R,8S)-3-allyl-6,7-bis(benzyloxy)-8-(benzyloxymethyl)hexahydropyrido[1,2-c][1,3]oxazin-1(3H)-one

: 1454313-47-3
(3S,4aR,6R,7R,8S)-6,7-bis(benzyloxy)-8-(benzyloxymethyl)-3-(dec-2-en-1-yl)hexahydropyrido[1,2-c][1,3]oxazin-1(3H)-one

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1002/ejoc.201201567

Reference yield:

: 55628-54-1
3,4,6-tri-O-benzyl-D-glucal

: 1454313-47-3
(3S,4aR,6R,7R,8S)-6,7-bis(benzyloxy)-8-(benzyloxymethyl)-3-(dec-2-en-1-yl)hexahydropyrido[1,2-c][1,3]oxazin-1(3H)-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: pyridinium chlorochromate; silica gel / dichloromethane / 12 h / Reflux

2.1: lithium hydroxide / methanol

3.1: diethyl ether / 0.5 h / 0 °C / Reflux

4.1: triphenylphosphine; hydrogen azide; diethylazodicarboxylate / tetrahydrofuran / 0 - 20 °C

5.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 48 h / 760.05 Torr

6.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C

6.2: 1 h / -78 °C

7.1: diisobutylaluminium hydride / dichloromethane; hexane / 0.5 h / -78 °C

7.2: -78 °C

8.1: 2,6-dimethylpyridine; osmium(VIII) oxide; sodium periodate / water; 1,4-dioxane / 2 h / 0 - 20 °C

9.1: diethyl ether; pentane / 19 h / -78 - 20 °C

9.2: 17 h / 20 °C

10.1: sodium hydride / tetrahydrofuran; mineral oil; N,N-dimethyl-formamide / 15 h / Reflux

11.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 24 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; hydrogen azide; palladium 10% on activated carbon; hydrogen; silica gel; sodium hydride; diisobutylaluminium hydride; triphenylphosphine; pyridinium chlorochromate; lithium hydroxide; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; mineral oil; pentane;
DOI:10.1002/ejoc.201201567

Reference yield:

: 1454313-45-1
benzyl (2S,3R,4R,6R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-6-[(2S)-2-hydroxypent-4-enyl]piperidine-1-carboxylate

: 1454313-47-3
(3S,4aR,6R,7R,8S)-6,7-bis(benzyloxy)-8-(benzyloxymethyl)-3-(dec-2-en-1-yl)hexahydropyrido[1,2-c][1,3]oxazin-1(3H)-one

Guidance literature:: Multi-step reaction with 2 steps

1: sodium hydride / tetrahydrofuran; mineral oil; N,N-dimethyl-formamide / 15 h / Reflux

2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 24 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1002/ejoc.201201567