(1R,2R,3S,4R,5R)-2,3,4-tris(benzyloxy)-8-oxa-6-azabicyclo[3.2.1]octane

Base Information

• Chemical Name: (1R,2R,3S,4R,5R)-2,3,4-tris(benzyloxy)-8-oxa-6-azabicyclo[3.2.1]octane
• CAS No.: 1354826-55-3
• Molecular Formula: C₂₇H₂₉NO₄
• Molecular Weight: 431.532
• Mol file: 1354826-55-3.mol

Synonyms:(1R,2R,3S,4R,5R)-2,3,4-tris(benzyloxy)-8-oxa-6-azabicyclo[3.2.1]octane

Chemical Property of (1R,2R,3S,4R,5R)-2,3,4-tris(benzyloxy)-8-oxa-6-azabicyclo[3.2.1]octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3S,4R,5R)-2,3,4-tris(benzyloxy)-8-oxa-6-azabicyclo[3.2.1]octane

There total 14 articles about (1R,2R,3S,4R,5R)-2,3,4-tris(benzyloxy)-8-oxa-6-azabicyclo[3.2.1]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:

6-azido-2,3,4-tri-O-benzyl-6-deoxy-α,β-D-glucopyranose → (1R,2R,3S,4R,5R)-2,3,4-tris(benzyloxy)-8-oxa-6-azabicyclo[3.2.1]octane (1354826-55-3)

Guidance literature:

With Triphenylphosphine polymer bound; In tetrahydrofuran; at 40 ℃; for 17h;

DOI:10.1016/j.bmc.2013.03.035

Reference yield:

β-D-glucose pentaacetate (604-69-3) → (1R,2R,3S,4R,5R)-2,3,4-tris(benzyloxy)-8-oxa-6-azabicyclo[3.2.1]octane (1354826-55-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / 0.17 h / 0 °C / Molecular sieve

1.2: 24 h / 0 - 20 °C / Molecular sieve

2.1: sodium; methanol / Petroleum ether / 1 h / 0 - 20 °C / Inert atmosphere

3.1: pyridine / 0 °C

4.1: sodium azide / N,N-dimethyl-formamide / 3 h / 80 °C

5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil; hexane / 0 - 20 °C / Inert atmosphere

5.2: 6 h / 20 °C / Inert atmosphere

6.1: (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; hydrogen / tetrahydrofuran / 6 h / 20 °C

6.2: 1 h / 20 °C

7.1: trimethylphosphane / tetrahydrofuran; toluene / 2 h / 90 °C

With pyridine; methanol; sodium azide; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; boron trifluoride diethyl etherate; hydrogen; sodium; sodium hydride; trimethylphosphane; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil; Petroleum ether;

DOI:10.1021/acs.orglett.0c00503

Reference yield:

Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-4-yl ester (10343-15-4,39698-55-0,54400-76-9,78730-32-2,119111-31-8,119111-32-9) → (1R,2R,3S,4R,5R)-2,3,4-tris(benzyloxy)-8-oxa-6-azabicyclo[3.2.1]octane (1354826-55-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium; methanol / Petroleum ether / 1 h / 0 - 20 °C / Inert atmosphere

2.1: pyridine / 0 °C

3.1: sodium azide / N,N-dimethyl-formamide / 3 h / 80 °C

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil; hexane / 0 - 20 °C / Inert atmosphere

4.2: 6 h / 20 °C / Inert atmosphere

5.1: (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; hydrogen / tetrahydrofuran / 6 h / 20 °C

5.2: 1 h / 20 °C

6.1: trimethylphosphane / tetrahydrofuran; toluene / 2 h / 90 °C

With pyridine; methanol; sodium azide; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; hydrogen; sodium; sodium hydride; trimethylphosphane; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; toluene; mineral oil; Petroleum ether;

DOI:10.1021/acs.orglett.0c00503

upstream raw materials:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

methyl 2,3,4-tri-O-benzyl-6-O-(4-methylbenzenesulfonyl)-α-D-glucopyranoside

(2R,3R,4S,5R,6S)-2-Azidomethyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran

benzaldehyde dimethyl acetal

Downstream raw materials:

(3R,4R,5R,6S,7S) 7-allyl-1-benzyl-4,5,6-tris(benzyloxy)azepan-3-ol

(2S,3R,4R,5S,6S)-6-allyl-1-benzyl-(3,4,5-tris(benzyloxy)piperidin-2-yl)methyl 4-nitrobenzoate

(3R,4R,5R,6S,7S)-7-allyl-1-benzyl-4,5,6-tris(benzyloxy)azepan-3-yl 4-nitrobenzoate

(3R,4R,5R,6S,7R)-1-benzyl-4,5,6-tris(benzyloxy)-7-vinylazepan-3-ol