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

Base Information

Chemical Name:3-O-acetyl-2,5-anhydro-6-O-benzoyl-5-C-[(benzoyloxy)methyl]-4-O-benzyl-D-allononitrile
CAS No.:904670-64-0
Molecular Formula:C₃₀H₂₇NO₈
Molecular Weight:529.546
Hs Code.:

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

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Chemical Property of 3-O-acetyl-2,5-anhydro-6-O-benzoyl-5-C-[(benzoyloxy)methyl]-4-O-benzyl-D-allononitrile

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Technology Process of 3-O-acetyl-2,5-anhydro-6-O-benzoyl-5-C-[(benzoyloxy)methyl]-4-O-benzyl-D-allononitrile

There total 1 articles about 3-O-acetyl-2,5-anhydro-6-O-benzoyl-5-C-[(benzoyloxy)methyl]-4-O-benzyl-D-allononitrile 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: 68.0%

: C₂₉H₂₆O₁₀

: 7677-24-9
trimethylsilyl cyanide

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

Guidance literature:: With boron trifluoride diethyl etherate; In acetonitrile; at 20 ℃; for 0.5h;
DOI:10.1002/ejoc.200500977

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:

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

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

Guidance literature:: Multi-step reaction with 8 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

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

6.2: 77 percent / MgO / tetrahydrofuran; H₂O / 1 h / 0 °C

7.1: 71 percent / TEA / CH₂Cl₂; acetonitrile / 1.5 h / 20 °C

8.1: 57 percent / DIPEA / CH₂Cl₂ / 1 h / 20 °C

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