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

Base Information

Chemical Name:2,5-anhydro-4-O-benzyl-1-[(tert-butoxycarbonyl)amino]-1-deoxy-5-C-(hydroxymethyl)-D-allitol
CAS No.:904670-65-1
Molecular Formula:C₁₉H₂₉NO₇
Molecular Weight:383.442
Hs Code.:

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

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Chemical Property of 2,5-anhydro-4-O-benzyl-1-[(tert-butoxycarbonyl)amino]-1-deoxy-5-C-(hydroxymethyl)-D-allitol

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Technology Process of 2,5-anhydro-4-O-benzyl-1-[(tert-butoxycarbonyl)amino]-1-deoxy-5-C-(hydroxymethyl)-D-allitol

There total 1 articles about 2,5-anhydro-4-O-benzyl-1-[(tert-butoxycarbonyl)amino]-1-deoxy-5-C-(hydroxymethyl)-D-allitol 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: 56.0%

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

: 24424-99-5
di-tert-butyl dicarbonate

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

Guidance literature:: 3-O-acetyl-2,5-anhydro-6-O-benzoyl-5-C-[(benzoyloxy)methyl]-4-O-benzyl-D-allononitrile; With dimethylsulfide borane complex; In tetrahydrofuran; at 20 ℃; for 16h;

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 0.5h;

di-tert-butyl dicarbonate; With sodium hydroxide; In ethanol; dichloromethane; at 20 ℃; for 16h;
DOI:10.1002/ejoc.200500977

Reference yield: 84.0%

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

: 98-88-4
benzoyl chloride

: 77-76-9
2,2-dimethoxy-propane

: 2,5-anhydro-3-O-benzoyl-4-O-benzyl-1-[(tert-butoxycarbonyl)amino]-1-deoxy-5-C-hydroxymethyl-6,5-(C-hydroxymethyl)-di-iso-propylidene-D-allitol

Guidance literature:: 2,5-anhydro-4-O-benzyl-1-[(tert-butoxycarbonyl)amino]-1-deoxy-5-C-(hydroxymethyl)-D-allitol; 2,2-dimethoxy-propane; With toluene-4-sulfonic acid; In tetrahydrofuran; at 20 ℃; for 2h;

benzoyl chloride; With TEA; In dichloromethane; at 20 ℃; for 16h;
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