(1R,4S,5S)-4-O-benzyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-tetrahydropyran-6-carboxylic acid

Base Information

Chemical Name:(1R,4S,5S)-4-O-benzyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-tetrahydropyran-6-carboxylic acid
CAS No.:742102-83-6
Molecular Formula:C₁₉H₂₇NO₆
Molecular Weight:365.426
Hs Code.:

Synonyms:(1R,4S,5S)-4-O-benzyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-tetrahydropyran-6-carboxylic acid

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Chemical Property of (1R,4S,5S)-4-O-benzyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-tetrahydropyran-6-carboxylic acid

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Technology Process of (1R,4S,5S)-4-O-benzyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-tetrahydropyran-6-carboxylic acid

There total 8 articles about (1R,4S,5S)-4-O-benzyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-tetrahydropyran-6-carboxylic acid 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: 100.0%

: 742102-80-3
2,3-dideoxy-4-O-benzyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-β-D-glucopyranose

: 742102-83-6
(1R,4S,5S)-4-O-benzyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-tetrahydropyran-6-carboxylic acid

Guidance literature:: With ruthenium trichloride; potassium hydroxide; dipotassium peroxodisulfate; In acetonitrile;
DOI:10.1021/jm049927q

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 742102-83-6
(1R,4S,5S)-4-O-benzyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-tetrahydropyran-6-carboxylic acid

Guidance literature:: Multi-step reaction with 5 steps

1: Et₃N / CH₂Cl₂

2: 0.60 g / NaOMe / methanol

3: 77 percent / (+)-camphorsulfonic acid / acetonitrile / 65 °C

4: DIBAL-H / toluene / 0 °C

5: 100 percent / aq. KOH; K₂S₂O₈; RuCl₃*3H₂O / acetonitrile

With ruthenium trichloride; potassium hydroxide; dipotassium peroxodisulfate; sodium methylate; diisobutylaluminium hydride; (+)-10-camphorsulfonic acid; triethylamine; In methanol; dichloromethane; toluene; acetonitrile;
DOI:10.1021/jm049927q

Reference yield:

: 229473-28-3
2,3-dideoxy-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-β-D-glucopyranose

: 742102-83-6
(1R,4S,5S)-4-O-benzyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-tetrahydropyran-6-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 77 percent / (+)-camphorsulfonic acid / acetonitrile / 65 °C

2: DIBAL-H / toluene / 0 °C

3: 100 percent / aq. KOH; K₂S₂O₈; RuCl₃*3H₂O / acetonitrile

With ruthenium trichloride; potassium hydroxide; dipotassium peroxodisulfate; diisobutylaluminium hydride; (+)-10-camphorsulfonic acid; In toluene; acetonitrile;
DOI:10.1021/jm049927q