2-{[N-(Benzyloxycarbonyl)glycyl]amino}-2-deoxy-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone

Base Information

• Chemical Name: 2-{[N-(Benzyloxycarbonyl)glycyl]amino}-2-deoxy-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone
• CAS No.: 172987-06-3
• Molecular Formula: C₂₃H₃₀N₂O₉
• Molecular Weight: 478.499

Synonyms:2-{[N-(Benzyloxycarbonyl)glycyl]amino}-2-deoxy-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone

Chemical Property of 2-{[N-(Benzyloxycarbonyl)glycyl]amino}-2-deoxy-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone

Chemical Property:

Purity/Quality:

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Technology Process of 2-{[N-(Benzyloxycarbonyl)glycyl]amino}-2-deoxy-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone

There total 4 articles about 2-{[N-(Benzyloxycarbonyl)glycyl]amino}-2-deoxy-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone 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%

N-(Benzyloxycarbonyl)glycine (1138-80-3) + (3aR,4R,7S,7aR)-7-Amino-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-one (153796-88-4) → 2-{[N-(Benzyloxycarbonyl)glycyl]amino}-2-deoxy-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone (172987-06-3)

Guidance literature:

With pyridine; chloroformic acid ethyl ester; In tetrahydrofuran; acetonitrile;

DOI:10.1016/0040-4039(95)01732-W

Reference yield:

2-azido-2-deoxy-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone (127903-44-0) → 2-{[N-(Benzyloxycarbonyl)glycyl]amino}-2-deoxy-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone (172987-06-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / H₂ / Pd / ethyl acetate

2: 86 percent / ethyl chloroformate, pyridine / acetonitrile; tetrahydrofuran

With pyridine; hydrogen; chloroformic acid ethyl ester; palladium; In tetrahydrofuran; ethyl acetate; acetonitrile;

DOI:10.1016/0040-4039(95)01732-W

Reference yield:

C13H15NO6 (55378-79-5) + (3aR,4R,7S,7aR)-7-Amino-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-one (153796-88-4) → 2-{[N-(Benzyloxycarbonyl)glycyl]amino}-2-deoxy-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone (172987-06-3)

Guidance literature:

With pyridine; In tetrahydrofuran; acetonitrile; at 0 - 20 ℃; for 2.5h;

DOI:10.1039/b009940f

upstream raw materials:

N-(Benzyloxycarbonyl)glycine

(3aR,4R,7S,7aR)-7-Amino-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-one

C₁₃H₁₅NO₆

2-azido-2-deoxy-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone

Downstream raw materials:

2-{[N-(Benzyloxycarbonyl)glycyl]amino}-2-deoxy-3,4-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone

(1R,4S,6R,7S,8S)-4-{[N-(Benzyloxycarbonyl)glycyl]amino}-6-hydroxymethyl-7,8-isopropylidenedioxy-2,5-dioxabicyclo[2.2.2]octan-3-one

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