(1R,5R)-6-exo,7-endo-dibenzoyloxy-N-methyl-8-exo-tosyloxy-3-oxa-2-azabicyclo<3.3.0>octane

Base Information

• Chemical Name: (1R,5R)-6-exo,7-endo-dibenzoyloxy-N-methyl-8-exo-tosyloxy-3-oxa-2-azabicyclo<3.3.0>octane
• CAS No.: 80685-07-0
• Molecular Formula: C₂₈H₂₇NO₈S
• Molecular Weight: 537.59

Synonyms:(1R,5R)-6-exo,7-endo-dibenzoyloxy-N-methyl-8-exo-tosyloxy-3-oxa-2-azabicyclo<3.3.0>octane

Chemical Property of (1R,5R)-6-exo,7-endo-dibenzoyloxy-N-methyl-8-exo-tosyloxy-3-oxa-2-azabicyclo<3.3.0>octane

Chemical Property:

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Technology Process of (1R,5R)-6-exo,7-endo-dibenzoyloxy-N-methyl-8-exo-tosyloxy-3-oxa-2-azabicyclo<3.3.0>octane

There total 2 articles about (1R,5R)-6-exo,7-endo-dibenzoyloxy-N-methyl-8-exo-tosyloxy-3-oxa-2-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: 73.0%

N-methylhydroxyamine hydrochloride (4229-44-1) + (2R,3S,4R)-3,4-bis-O-benzoyloxy-2-O-toluene-p-sulfonylhex-5-enal (80675-62-3) → (1R,5R)-6-exo,7-endo-dibenzoyloxy-N-methyl-8-exo-tosyloxy-3-oxa-2-azabicyclo<3.3.0>octane (80685-07-0)

Guidance literature:

With pyridine; In ethanol; at 45 ℃; for 2h;

Reference yield:

3,4-di-O-benzoyl-6-deoxy-6-iodo-2-O-p-toluenesulfonyl-α-D-glucopyranoside (34340-09-5) → (1R,5R)-6-exo,7-endo-dibenzoyloxy-N-methyl-8-exo-tosyloxy-3-oxa-2-azabicyclo<3.3.0>octane (80685-07-0)

Guidance literature:

Multi-step reaction with 2 steps

1: Zn / ethanol / Heating

2: ethanol; pyridine / 45 °C

With zinc; In pyridine; ethanol;

DOI:10.1039/c39810000983

Reference yield: 74.0%

(1R,5R)-6-exo,7-endo-dibenzoyloxy-N-methyl-8-exo-tosyloxy-3-oxa-2-azabicyclo<3.3.0>octane (80685-07-0) → (1R)-2-endo,3-exo-dibenzoyloxy-4-endo-hydroxymethyl-N-methyl-6-azabicyclo<3.1.0>hexane (80675-63-4)

Guidance literature:

With hydrogen; W-2 Raney nickel; In ethyl acetate; for 4h;

upstream raw materials:

N-methylhydroxyamine hydrochloride

(2R,3S,4R)-3,4-bis-O-benzoyloxy-2-O-toluene-p-sulfonylhex-5-enal

3,4-di-O-benzoyl-6-deoxy-6-iodo-2-O-p-toluenesulfonyl-α-D-glucopyranoside

Downstream raw materials:

(1R)-2-endo,3-exo-dibenzoyloxy-4-endo-hydroxymethyl-N-methyl-6-azabicyclo<3.1.0>hexane

(3R,4R,5R)-3,4-dibenzoyloxy-5-(hydroxymethyl)cyclopent-1-ene

(1S,2S,4R,6S)-8-oxo-3,7-dioxatricyclo<4.3.0.0^2,4>nonane

C₂₁H₁₇NO₄

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