(1R,3S,4S,7S)-1-[(4,4'-dimethoxytrityl)oxymethyl]-3-{[(fluorenylmethoxy)carbonylamino]methyl}-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane

Base Information

Chemical Name:(1R,3S,4S,7S)-1-[(4,4'-dimethoxytrityl)oxymethyl]-3-{[(fluorenylmethoxy)carbonylamino]methyl}-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane
CAS No.:904670-71-9
Molecular Formula:C₄₃H₄₁NO₈
Molecular Weight:699.8
Hs Code.:

Synonyms:(1R,3S,4S,7S)-1-[(4,4'-dimethoxytrityl)oxymethyl]-3-{[(fluorenylmethoxy)carbonylamino]methyl}-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane

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Chemical Property of (1R,3S,4S,7S)-1-[(4,4'-dimethoxytrityl)oxymethyl]-3-{[(fluorenylmethoxy)carbonylamino]methyl}-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane

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Technology Process of (1R,3S,4S,7S)-1-[(4,4'-dimethoxytrityl)oxymethyl]-3-{[(fluorenylmethoxy)carbonylamino]methyl}-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane

There total 7 articles about (1R,3S,4S,7S)-1-[(4,4'-dimethoxytrityl)oxymethyl]-3-{[(fluorenylmethoxy)carbonylamino]methyl}-7-hydroxy-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: 71.0%

: 904670-70-8
(1S,3S,4S,7S)-3-{[(fluorenylmethoxy)carbonyl]aminomethyl}-7-hydroxy-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptane

: 40615-36-9
4,4'-dimethoxytrityl chloride

: 904670-71-9
(1R,3S,4S,7S)-1-[(4,4'-dimethoxytrityl)oxymethyl]-3-{[(fluorenylmethoxy)carbonylamino]methyl}-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: With TEA; In dichloromethane; acetonitrile; at 20 ℃; for 1.5h;
DOI:10.1002/ejoc.200500977

Reference yield:

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

: 904670-71-9
(1R,3S,4S,7S)-1-[(4,4'-dimethoxytrityl)oxymethyl]-3-{[(fluorenylmethoxy)carbonylamino]methyl}-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 2 steps

1.1: H₂ / Pd/C / ethanol / 14 h / 20 °C

1.2: 77 percent / MgO / tetrahydrofuran; H₂O / 1 h / 0 °C

2.1: 71 percent / TEA / CH₂Cl₂; acetonitrile / 1.5 h / 20 °C

With TEA; hydrogen; palladium on activated charcoal; In ethanol; dichloromethane; acetonitrile;
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

: 904670-71-9
(1R,3S,4S,7S)-1-[(4,4'-dimethoxytrityl)oxymethyl]-3-{[(fluorenylmethoxy)carbonylamino]methyl}-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 6 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: H₂ / Pd/C / ethanol / 14 h / 20 °C

5.2: 77 percent / MgO / tetrahydrofuran; H₂O / 1 h / 0 °C

6.1: 71 percent / TEA / CH₂Cl₂; acetonitrile / 1.5 h / 20 °C

With sodium hydroxide; TEA; hydrogen; toluene-4-sulfonic acid; sodium phenyl-methanolate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/ejoc.200500977