(1S,3S,4S,7S)-7-benzyloxy-3-[(tert-butoxycarbonyl)aminomethyl]-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptane

Base Information

Chemical Name:(1S,3S,4S,7S)-7-benzyloxy-3-[(tert-butoxycarbonyl)aminomethyl]-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptane
CAS No.:904670-69-5
Molecular Formula:C₁₉H₂₇NO₆
Molecular Weight:365.426
Hs Code.:

Synonyms:(1S,3S,4S,7S)-7-benzyloxy-3-[(tert-butoxycarbonyl)aminomethyl]-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptane

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Chemical Property of (1S,3S,4S,7S)-7-benzyloxy-3-[(tert-butoxycarbonyl)aminomethyl]-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptane

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Technology Process of (1S,3S,4S,7S)-7-benzyloxy-3-[(tert-butoxycarbonyl)aminomethyl]-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptane

There total 6 articles about (1S,3S,4S,7S)-7-benzyloxy-3-[(tert-butoxycarbonyl)aminomethyl]-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptane 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%

: 904670-68-4
(1R,3S,4S,7S)-7-benzyloxy-3-[(tert-butoxycarbonyl)aminomethyl]-1-[(methylsulfonyloxy)methyl]-2,5-dioxabicyclo[2.2.1]heptane

: 904670-69-5
(1S,3S,4S,7S)-7-benzyloxy-3-[(tert-butoxycarbonyl)aminomethyl]-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: With sodium phenyl-methanolate; In N,N-dimethyl-formamide; at 100 ℃; for 14h;
DOI:10.1002/ejoc.200500977

Reference yield:

: 904670-65-1
2,5-anhydro-4-O-benzyl-1-[(tert-butoxycarbonyl)amino]-1-deoxy-5-C-(hydroxymethyl)-D-allitol

: 904670-69-5
(1S,3S,4S,7S)-7-benzyloxy-3-[(tert-butoxycarbonyl)aminomethyl]-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 4 steps

1.1: p-toluenesulfonic acid / tetrahydrofuran / 2 h / 20 °C

1.2: 84 percent / TEA / CH₂Cl₂ / 16 h / 20 °C

2.1: p-toluenesulfonic acid / methanol / 0.75 h

2.2: 73 percent / TEA / CH₂Cl₂ / 3.5 h

3.1: 84 percent / aq. NaOH / tetrahydrofuran / 16 h / 20 °C

4.1: 73 percent / NaOBz / dimethylformamide / 14 h / 100 °C

With sodium hydroxide; toluene-4-sulfonic acid; sodium phenyl-methanolate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200500977

Reference yield:

: 904670-64-0
3-O-acetyl-2,5-anhydro-6-O-benzoyl-5-C-[(benzoyloxy)methyl]-4-O-benzyl-D-allononitrile

: 904670-69-5
(1S,3S,4S,7S)-7-benzyloxy-3-[(tert-butoxycarbonyl)aminomethyl]-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 5 steps

1.1: BH₃*S(Me)2 / tetrahydrofuran / 16 h / 20 °C

1.2: aq. HCl / tetrahydrofuran / 0.5 h / 20 °C

1.3: 56 percent / aq. NaOH / ethanol; CH₂Cl₂ / 16 h / 20 °C

2.1: p-toluenesulfonic acid / tetrahydrofuran / 2 h / 20 °C

2.2: 84 percent / TEA / CH₂Cl₂ / 16 h / 20 °C

3.1: p-toluenesulfonic acid / methanol / 0.75 h

3.2: 73 percent / TEA / CH₂Cl₂ / 3.5 h

4.1: 84 percent / aq. NaOH / tetrahydrofuran / 16 h / 20 °C

5.1: 73 percent / NaOBz / dimethylformamide / 14 h / 100 °C

With sodium hydroxide; dimethylsulfide borane complex; toluene-4-sulfonic acid; sodium phenyl-methanolate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200500977