(1S)-N-benzyl-2-exo,3-endo-2,3-dihydroxy-4-endo-4-hydroxymethyl-6-azabicyclo[3.1.0]hexane

Base Information

Chemical Name:(1S)-N-benzyl-2-exo,3-endo-2,3-dihydroxy-4-endo-4-hydroxymethyl-6-azabicyclo[3.1.0]hexane
CAS No.:540776-28-1
Molecular Formula:C₁₃H₁₇NO₃
Molecular Weight:235.283
Hs Code.:

Synonyms:(1S)-N-benzyl-2-exo,3-endo-2,3-dihydroxy-4-endo-4-hydroxymethyl-6-azabicyclo[3.1.0]hexane

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Chemical Property of (1S)-N-benzyl-2-exo,3-endo-2,3-dihydroxy-4-endo-4-hydroxymethyl-6-azabicyclo[3.1.0]hexane

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Technology Process of (1S)-N-benzyl-2-exo,3-endo-2,3-dihydroxy-4-endo-4-hydroxymethyl-6-azabicyclo[3.1.0]hexane

There total 8 articles about (1S)-N-benzyl-2-exo,3-endo-2,3-dihydroxy-4-endo-4-hydroxymethyl-6-azabicyclo[3.1.0]hexane 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%

: 540776-26-9
(1S)-N-benzyl-2-exo,3-endo-2,3-bis(benzoyloxy)-4-endo-4-hydroxymethyl-6-azabicyclo[3.1.0]hexane

: 540776-28-1
(1S)-N-benzyl-2-exo,3-endo-2,3-dihydroxy-4-endo-4-hydroxymethyl-6-azabicyclo[3.1.0]hexane

Guidance literature:: With sodium methylate; In methanol; at 20 ℃; for 4h; pH=10;
DOI:10.1039/b210038j

Reference yield:

: 540776-16-7
(2'S,3'S)-methyl 3,4-O-[2',3'-dimethoxybutane-2',3'-diyl]-2,6-bis(O-toluene-p-sulfonyl)-α-D-mannopyranoside

: 540776-28-1
(1S)-N-benzyl-2-exo,3-endo-2,3-dihydroxy-4-endo-4-hydroxymethyl-6-azabicyclo[3.1.0]hexane

Guidance literature:: Multi-step reaction with 7 steps

1: 74 percent / NaI; Ac₂O / 1.5 h / Heating

2: aq. TFA / 1.5 h / 20 °C

3: 2.62 g / pyridine / 24 h / 20 °C

4: Zn / aq. ethanol / 1 h / Heating

5: 146 mg / CaCO₃ / toluene / 1.5 h / 50 °C

6: 46 percent / H₂ / Raney nickel / ethyl acetate; ethanol / 18 h / 20 °C / 760.05 Torr

7: 73 percent / NaOMe / methanol / 4 h / 20 °C / pH 10

With pyridine; hydrogen; sodium methylate; acetic anhydride; trifluoroacetic acid; calcium carbonate; sodium iodide; zinc; nickel; In methanol; ethanol; ethyl acetate; toluene;
DOI:10.1039/b210038j

Reference yield:

: 617-04-9
(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

: 540776-28-1
(1S)-N-benzyl-2-exo,3-endo-2,3-dihydroxy-4-endo-4-hydroxymethyl-6-azabicyclo[3.1.0]hexane

Guidance literature:: Multi-step reaction with 9 steps

1: (+/-)-camphorsulfonic acid / methanol / 16 h / Heating

2: 8.85 g / pyridine / 24 h / 20 °C

3: 74 percent / NaI; Ac₂O / 1.5 h / Heating

4: aq. TFA / 1.5 h / 20 °C

5: 2.62 g / pyridine / 24 h / 20 °C

6: Zn / aq. ethanol / 1 h / Heating

7: 146 mg / CaCO₃ / toluene / 1.5 h / 50 °C

8: 46 percent / H₂ / Raney nickel / ethyl acetate; ethanol / 18 h / 20 °C / 760.05 Torr

9: 73 percent / NaOMe / methanol / 4 h / 20 °C / pH 10

With pyridine; camphor-10-sulfonic acid; hydrogen; sodium methylate; acetic anhydride; trifluoroacetic acid; calcium carbonate; sodium iodide; zinc; nickel; In methanol; ethanol; ethyl acetate; toluene;
DOI:10.1039/b210038j