(3aR,4R,6aR)-N-benzyl-tetrahydro-N-hydroxy-2,2-dimethylfuro[3,4-d]-1,3-dioxol-4-amine

Base Information

• Chemical Name: (3aR,4R,6aR)-N-benzyl-tetrahydro-N-hydroxy-2,2-dimethylfuro[3,4-d]-1,3-dioxol-4-amine
• CAS No.: 444911-54-0
• Molecular Formula: C₁₄H₁₉NO₄
• Molecular Weight: 265.309

Synonyms:(3aR,4R,6aR)-N-benzyl-tetrahydro-N-hydroxy-2,2-dimethylfuro[3,4-d]-1,3-dioxol-4-amine

Chemical Property of (3aR,4R,6aR)-N-benzyl-tetrahydro-N-hydroxy-2,2-dimethylfuro[3,4-d]-1,3-dioxol-4-amine

Chemical Property:

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Technology Process of (3aR,4R,6aR)-N-benzyl-tetrahydro-N-hydroxy-2,2-dimethylfuro[3,4-d]-1,3-dioxol-4-amine

There total 2 articles about (3aR,4R,6aR)-N-benzyl-tetrahydro-N-hydroxy-2,2-dimethylfuro[3,4-d]-1,3-dioxol-4-amine 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: 88.0%

2,3-O-isopropylidene-D-erythrose (189996-60-9) + N-benzyl hydroxylalmine (622-30-0) → (3aR,4R,6aR)-N-benzyl-tetrahydro-N-hydroxy-2,2-dimethylfuro[3,4-d]-1,3-dioxol-4-amine (444911-54-0)

Guidance literature:

With pyridine; 3 A molecular sieve; at 20 ℃;

DOI:10.1016/S0040-4039(02)00372-6

Reference yield:

2,3-O-isopropylidene-D-erythrose (189996-60-9) + N-benzylhydroxylamine hydrochloride (29601-98-7) → (3aR,4R,6aR)-N-benzyl-tetrahydro-N-hydroxy-2,2-dimethylfuro[3,4-d]-1,3-dioxol-4-amine (444911-54-0) + C14H19NO4

Guidance literature:

In pyridine; at 20 ℃;

DOI:10.1002/ejoc.200300353

Reference yield: 97.0%

(3aR,4R,6aR)-N-benzyl-tetrahydro-N-hydroxy-2,2-dimethylfuro[3,4-d]-1,3-dioxol-4-amine (444911-54-0) → (3aR,4R,6aR)-tetrahydro-2,2-dimethyl-N-(phenylmethylene)furo[3,4-d]-1,3-dioxol-4-amine N-oxide (444911-56-2)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1002/ejoc.200300353

upstream raw materials:

2,3-O-isopropylidene-D-erythrose

N-benzyl hydroxylalmine

N-benzylhydroxylamine hydrochloride

Downstream raw materials:

(3aR,4R,6aR)-tetrahydro-2,2-dimethyl-N-(phenylmethylene)furo[3,4-d]-1,3-dioxol-4-amine N-oxide

(2R,3S,4R)-4-N-benzylhydroxylamino-2,3-O-isopropylidene-4-(2-thiazolyl)-1,2,3-butanetriol

(2R,3S,4S)-4-N-benzylhydroxylamino-2,3-O-isopropylidene-5-vinyl-1,2,3-pentanetriol

dimethyl (3R,4S,5R)-2-[(3aR,4R,6aR)-tetrahydro-2,2-dimethyl-3-phenylfuro[3,4-d][1,3]dioxol-4-yl]isoxazolidine-4,5-dicarboxylate

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