(1R,5S,6S,4'S)-7-benzyloxycarbonyl-3,3-dimethyl-6-4'-2',2'-dimethyl-1',3'-dioxanyl-2,4-dioxa-7-azabicyclo<3.3.0>octane

Base Information

• Chemical Name: (1R,5S,6S,4'S)-7-benzyloxycarbonyl-3,3-dimethyl-6-4'-2',2'-dimethyl-1',3'-dioxanyl-2,4-dioxa-7-azabicyclo<3.3.0>octane
• CAS No.: 105878-89-5
• Molecular Formula: C₂₀H₂₇NO₆
• Molecular Weight: 377.437
• Mol file: 105878-89-5.mol

Synonyms:(1R,5S,6S,4'S)-7-benzyloxycarbonyl-3,3-dimethyl-6-4'-2',2'-dimethyl-1',3'-dioxanyl-2,4-dioxa-7-azabicyclo<3.3.0>octane

Chemical Property of (1R,5S,6S,4'S)-7-benzyloxycarbonyl-3,3-dimethyl-6-4'-2',2'-dimethyl-1',3'-dioxanyl-2,4-dioxa-7-azabicyclo<3.3.0>octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,5S,6S,4'S)-7-benzyloxycarbonyl-3,3-dimethyl-6-4'-2',2'-dimethyl-1',3'-dioxanyl-2,4-dioxa-7-azabicyclo<3.3.0>octane

There total 4 articles about (1R,5S,6S,4'S)-7-benzyloxycarbonyl-3,3-dimethyl-6-4'-2',2'-dimethyl-1',3'-dioxanyl-2,4-dioxa-7-azabicyclo<3.3.0>octane 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: 54.0%

Methanesulfonic acid (R)-[(4R,5R)-5-(benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester (98362-00-6) → (1R,5S,6S,4'S)-7-benzyloxycarbonyl-3,3-dimethyl-6-4'-2',2'-dimethyl-1',3'-dioxanyl-2,4-dioxa-7-azabicyclo<3.3.0>octane (105878-89-5)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; paraffin; at 70 ℃; for 6h;

DOI:10.1248/cpb.35.3995

Reference yield:

1,4-Dideoxy-2,3:5,6-di-O-isopropylidene-1,4-imino-D-talitol (117781-05-2) + benzyl chloroformate (501-53-1,94274-21-2) → (1R,5S,6S,4'S)-7-benzyloxycarbonyl-3,3-dimethyl-6-4'-2',2'-dimethyl-1',3'-dioxanyl-2,4-dioxa-7-azabicyclo<3.3.0>octane (105878-89-5)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1039/c6ob00531d

Reference yield:

N-hydroxyl-2,3,5,6-di-O-isopropylidene-1,4-dideoxy-1,4-imino-D-talitol → (1R,5S,6S,4'S)-7-benzyloxycarbonyl-3,3-dimethyl-6-4'-2',2'-dimethyl-1',3'-dioxanyl-2,4-dioxa-7-azabicyclo<3.3.0>octane (105878-89-5)

Guidance literature:

Multi-step reaction with 2 steps

1: zinc; copper(II) acetate monohydrate; acetic acid / 20 °C

2: sodium hydrogencarbonate / tetrahydrofuran; water / 20 °C

With copper(II) acetate monohydrate; sodium hydrogencarbonate; acetic acid; zinc; In tetrahydrofuran; water;

DOI:10.1039/c6ob00531d

upstream raw materials:

Methanesulfonic acid (R)-[(4R,5R)-5-(benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester

1,4-Dideoxy-2,3:5,6-di-O-isopropylidene-1,4-imino-D-talitol

benzyl chloroformate

Downstream raw materials:

(1R,5S,6S,1'S)-7-benzyloxycarbonyl-6-1',2'-dihydroxyethyl-3,3-dimethyl-2,4-dioxa-7-azabicyclo<3.3.0>octane

(1S,2R,8R,8aS)-octahydro-1,2,8-indolizidinetriol

(2S,3S,4R,1'S)-3,4-dihydroxy-2-1',2'-dihydroxyethylpyrrolidine