(3aS,4R,7aS)-1-Benzyl-4-hydroxymethyl-1,3a,4,7a-tetrahydro-pyrano[4,3-d]oxazol-2-one

Base Information

Chemical Name:(3aS,4R,7aS)-1-Benzyl-4-hydroxymethyl-1,3a,4,7a-tetrahydro-pyrano[4,3-d]oxazol-2-one
CAS No.:160849-58-1
Molecular Formula:C₁₄H₁₅NO₄
Molecular Weight:261.277
Hs Code.:

Synonyms:(3aS,4R,7aS)-1-Benzyl-4-hydroxymethyl-1,3a,4,7a-tetrahydro-pyrano[4,3-d]oxazol-2-one

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Chemical Property of (3aS,4R,7aS)-1-Benzyl-4-hydroxymethyl-1,3a,4,7a-tetrahydro-pyrano[4,3-d]oxazol-2-one

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Technology Process of (3aS,4R,7aS)-1-Benzyl-4-hydroxymethyl-1,3a,4,7a-tetrahydro-pyrano[4,3-d]oxazol-2-one

There total 7 articles about (3aS,4R,7aS)-1-Benzyl-4-hydroxymethyl-1,3a,4,7a-tetrahydro-pyrano[4,3-d]oxazol-2-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: 96.0%

: 174148-49-3
(3aS,4R,7aS)-1-Benzyl-4-triisopropylsilanyloxymethyl-1,3a,4,7a-tetrahydro-pyrano[4,3-d]oxazol-2-one

: 160849-58-1
(3aS,4R,7aS)-1-Benzyl-4-hydroxymethyl-1,3a,4,7a-tetrahydro-pyrano[4,3-d]oxazol-2-one

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1021/ja00062a057

Reference yield:

: 137915-37-8
1,2-dideoxy-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose

: 160849-58-1
(3aS,4R,7aS)-1-Benzyl-4-hydroxymethyl-1,3a,4,7a-tetrahydro-pyrano[4,3-d]oxazol-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) NaH / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) CH₂Cl₂, RT, overnight

2: BF₃*Et₂O / CH₂Cl₂ / 5 h / -78 °C

3: 80 percent / TsOH*H₂O, Py / H₂O / 14 h / 80 °C

4: 1.) NaH, tetrabutylammonium iodide / 1.) DMF, 2.) DMF, RT

5: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h

With pyridine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ja952907g

Reference yield:

: 148302-24-3
3-amino-1,5-anhydro-2,3-dideoxy-3,O,4,N-<(trichloromethyl)oxazolino>-6-O-(triisopropylsilyl)-D-ribo-hex-1-enopyranose

: 160849-58-1
(3aS,4R,7aS)-1-Benzyl-4-hydroxymethyl-1,3a,4,7a-tetrahydro-pyrano[4,3-d]oxazol-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: 80 percent / TsOH*H₂O, Py / H₂O / 14 h / 80 °C

2: 1.) NaH, tetrabutylammonium iodide / 1.) DMF, 2.) DMF, RT

3: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h

With pyridine; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; water;
DOI:10.1021/ja952907g