(4R,5S,6R)-N-tert-butoxycarbonyl-5-O-benzyl-6,7-O-isopropylidene-2,3-dideoxy-heptono-1,4-lactam

Base Information

Chemical Name:(4R,5S,6R)-N-tert-butoxycarbonyl-5-O-benzyl-6,7-O-isopropylidene-2,3-dideoxy-heptono-1,4-lactam
CAS No.:141293-22-3
Molecular Formula:C₂₂H₃₁NO₆
Molecular Weight:405.491
Hs Code.:

Synonyms:(4R,5S,6R)-N-tert-butoxycarbonyl-5-O-benzyl-6,7-O-isopropylidene-2,3-dideoxy-heptono-1,4-lactam

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Chemical Property of (4R,5S,6R)-N-tert-butoxycarbonyl-5-O-benzyl-6,7-O-isopropylidene-2,3-dideoxy-heptono-1,4-lactam

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Technology Process of (4R,5S,6R)-N-tert-butoxycarbonyl-5-O-benzyl-6,7-O-isopropylidene-2,3-dideoxy-heptono-1,4-lactam

There total 5 articles about (4R,5S,6R)-N-tert-butoxycarbonyl-5-O-benzyl-6,7-O-isopropylidene-2,3-dideoxy-heptono-1,4-lactam 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%

: 100-39-0
benzyl bromide

: 141293-21-2
(1'S,4''R,5R)-1-(tert-butoxycarbonyl)-5-[(2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl]pyrrolidin-2-one

: 141293-22-3
(4R,5S,6R)-N-tert-butoxycarbonyl-5-O-benzyl-6,7-O-isopropylidene-2,3-dideoxy-heptono-1,4-lactam

Guidance literature:: With silver(l) oxide; In tetrahydrofuran; for 5h; Ambient temperature;
DOI:10.1016/S0957-4166(00)86037-1

Reference yield:

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

: 141293-22-3
(4R,5S,6R)-N-tert-butoxycarbonyl-5-O-benzyl-6,7-O-isopropylidene-2,3-dideoxy-heptono-1,4-lactam

Guidance literature:: Multi-step reaction with 5 steps

1: DMAP / acetonitrile / Ambient temperature

2: 2,6-lutidine / CH₂Cl₂ / Ambient temperature

3: 80 percent / SnCl₄ / diethyl ether; CH₂Cl₂ / 3 h / -85 °C

4: 92 percent / H₂, NaOAc / 10percent Pd/C / tetrahydrofuran / 24 h / Ambient temperature

5: 88 percent / Ag₂O / tetrahydrofuran / 5 h / Ambient temperature

With 2,6-dimethylpyridine; dmap; hydrogen; sodium acetate; tin(IV) chloride; silver(l) oxide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;
DOI:10.1016/S0957-4166(00)86037-1

Reference yield:

: 141293-14-3
N-(tert-butoxycarbonyl)pyrrol-2(5H)-one

: 141293-22-3
(4R,5S,6R)-N-tert-butoxycarbonyl-5-O-benzyl-6,7-O-isopropylidene-2,3-dideoxy-heptono-1,4-lactam

Guidance literature:: Multi-step reaction with 4 steps

1: 2,6-lutidine / CH₂Cl₂ / Ambient temperature

2: 80 percent / SnCl₄ / diethyl ether; CH₂Cl₂ / 3 h / -85 °C

3: 92 percent / H₂, NaOAc / 10percent Pd/C / tetrahydrofuran / 24 h / Ambient temperature

4: 88 percent / Ag₂O / tetrahydrofuran / 5 h / Ambient temperature

With 2,6-dimethylpyridine; hydrogen; sodium acetate; tin(IV) chloride; silver(l) oxide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/S0957-4166(00)86037-1