(1S,3S,4S,7S)-7-benzyloxy-3-{[(fluorenylmethoxy)carbonylamino]methyl}-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptane

Base Information

Chemical Name:(1S,3S,4S,7S)-7-benzyloxy-3-{[(fluorenylmethoxy)carbonylamino]methyl}-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptane
CAS No.:904670-73-1
Molecular Formula:C₂₉H₂₉NO₆
Molecular Weight:487.552
Hs Code.:

Synonyms:(1S,3S,4S,7S)-7-benzyloxy-3-{[(fluorenylmethoxy)carbonylamino]methyl}-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptane

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Chemical Property of (1S,3S,4S,7S)-7-benzyloxy-3-{[(fluorenylmethoxy)carbonylamino]methyl}-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptane

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Technology Process of (1S,3S,4S,7S)-7-benzyloxy-3-{[(fluorenylmethoxy)carbonylamino]methyl}-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptane

There total 6 articles about (1S,3S,4S,7S)-7-benzyloxy-3-{[(fluorenylmethoxy)carbonylamino]methyl}-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: 86.0%

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

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 904670-73-1
(1S,3S,4S,7S)-7-benzyloxy-3-{[(fluorenylmethoxy)carbonylamino]methyl}-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: (1S,3S,4S,7S)-7-benzyloxy-3-[(tert-butoxycarbonyl)aminomethyl]-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptane; With trifluoroacetic acid; for 0.5h;

(fluorenylmethoxy)carbonyl chloride; With magnesium oxide; In tetrahydrofuran; water; at 0 ℃; for 1h;
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

: 904670-73-1
(1S,3S,4S,7S)-7-benzyloxy-3-{[(fluorenylmethoxy)carbonylamino]methyl}-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 5 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

5.1: TFA / 0.5 h

5.2: 86 percent / MgO / tetrahydrofuran; H₂O / 1 h / 0 °C

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

Reference yield:

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

: 904670-73-1
(1S,3S,4S,7S)-7-benzyloxy-3-{[(fluorenylmethoxy)carbonylamino]methyl}-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 2 steps

1.1: 73 percent / NaOBz / dimethylformamide / 14 h / 100 °C

2.1: TFA / 0.5 h

2.2: 86 percent / MgO / tetrahydrofuran; H₂O / 1 h / 0 °C

With sodium phenyl-methanolate; trifluoroacetic acid; In N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200500977