(4S,6R)-4-benzyloxycarbonyl-3-tert-butoxycarbonyl-6-hydroxymethyl-tetrahydro-2H-1,3-oxazine

Base Information

Chemical Name:(4S,6R)-4-benzyloxycarbonyl-3-tert-butoxycarbonyl-6-hydroxymethyl-tetrahydro-2H-1,3-oxazine
CAS No.:911225-61-1
Molecular Formula:C₁₈H₂₅NO₆
Molecular Weight:351.4
Hs Code.:

Synonyms:(4S,6R)-4-benzyloxycarbonyl-3-tert-butoxycarbonyl-6-hydroxymethyl-tetrahydro-2H-1,3-oxazine

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Chemical Property of (4S,6R)-4-benzyloxycarbonyl-3-tert-butoxycarbonyl-6-hydroxymethyl-tetrahydro-2H-1,3-oxazine

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Technology Process of (4S,6R)-4-benzyloxycarbonyl-3-tert-butoxycarbonyl-6-hydroxymethyl-tetrahydro-2H-1,3-oxazine

There total 4 articles about (4S,6R)-4-benzyloxycarbonyl-3-tert-butoxycarbonyl-6-hydroxymethyl-tetrahydro-2H-1,3-oxazine 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: 86.0%

: 6-(tert-butyl-diphenyl-silanyloxymethyl)-[1,3]oxazinane-3,4-dicarboxylic acid 4-benzyl ester 3-tert-butyl ester

: 911225-61-1
(4S,6R)-4-benzyloxycarbonyl-3-tert-butoxycarbonyl-6-hydroxymethyl-tetrahydro-2H-1,3-oxazine

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 12h;
DOI:10.1016/j.tet.2006.06.105

Reference yield:

: 911225-59-7
(4S,6R)-6-tert-butyldiphenylsilyloxymethyl-4-methoxycarbonyl-tetrahydro-2H-1,3-oxazine

: 911225-61-1
(4S,6R)-4-benzyloxycarbonyl-3-tert-butoxycarbonyl-6-hydroxymethyl-tetrahydro-2H-1,3-oxazine

Guidance literature:: Multi-step reaction with 3 steps

1: 81 percent / triethylamine / dioxane / 12 h / 20 °C

2: Ti(O-iPr)4 / benzene / 12 h / Heating

3: 86 percent / TBAF / tetrahydrofuran / 12 h / 20 °C

With titanium(IV) isopropylate; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; 1,4-dioxane; benzene;
DOI:10.1016/j.tet.2006.06.105

Reference yield:

: (4S,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-[1,3]oxazinane-4-carboxylic acid

: 911225-61-1
(4S,6R)-4-benzyloxycarbonyl-3-tert-butoxycarbonyl-6-hydroxymethyl-tetrahydro-2H-1,3-oxazine

Guidance literature:: Multi-step reaction with 4 steps

1: 0.473 g / diethyl ether

2: 81 percent / triethylamine / dioxane / 12 h / 20 °C

3: Ti(O-iPr)4 / benzene / 12 h / Heating

4: 86 percent / TBAF / tetrahydrofuran / 12 h / 20 °C

With titanium(IV) isopropylate; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; 1,4-dioxane; diethyl ether; benzene;
DOI:10.1016/j.tet.2006.06.105