2-O-allyl-3-O-benzyl-N-(tert-butoxycarbonyl)-1,5-dideoxy-1,5-imino-4,6-O-(4-methoxybenzylidene)-D-glucitol

Base Information

Chemical Name:2-O-allyl-3-O-benzyl-N-(tert-butoxycarbonyl)-1,5-dideoxy-1,5-imino-4,6-O-(4-methoxybenzylidene)-D-glucitol
CAS No.:945395-01-7
Molecular Formula:C₂₉H₃₇NO₇
Molecular Weight:511.615
Hs Code.:

Synonyms:2-O-allyl-3-O-benzyl-N-(tert-butoxycarbonyl)-1,5-dideoxy-1,5-imino-4,6-O-(4-methoxybenzylidene)-D-glucitol

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Chemical Property of 2-O-allyl-3-O-benzyl-N-(tert-butoxycarbonyl)-1,5-dideoxy-1,5-imino-4,6-O-(4-methoxybenzylidene)-D-glucitol

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Technology Process of 2-O-allyl-3-O-benzyl-N-(tert-butoxycarbonyl)-1,5-dideoxy-1,5-imino-4,6-O-(4-methoxybenzylidene)-D-glucitol

There total 14 articles about 2-O-allyl-3-O-benzyl-N-(tert-butoxycarbonyl)-1,5-dideoxy-1,5-imino-4,6-O-(4-methoxybenzylidene)-D-glucitol 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: 99.0%

: 945394-95-6
3-O-benzyl-N-(tert-butoxycarbonyl)-1,5-dideoxy-1,5-imino-4,6-O-(4-methoxybenzylidene)-D-glucitol

: 106-95-6
allyl bromide

: 945395-01-7
2-O-allyl-3-O-benzyl-N-(tert-butoxycarbonyl)-1,5-dideoxy-1,5-imino-4,6-O-(4-methoxybenzylidene)-D-glucitol

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃;
DOI:10.1016/j.tet.2007.04.070

Reference yield:

: 945394-84-3
6-azido-6-deoxy-1-O-benzyl-2,3-O-isopropylidene-α-L-sorbofuranose

: 945395-01-7
2-O-allyl-3-O-benzyl-N-(tert-butoxycarbonyl)-1,5-dideoxy-1,5-imino-4,6-O-(4-methoxybenzylidene)-D-glucitol

Guidance literature:: Multi-step reaction with 9 steps

1.1: 92 percent / H₂O; Dowex-50-X₈-100 (H⁽¹⁺⁾) / acetonitrile / 3 h / Heating

2.1: H₂ / Pd(OH)2/C / methanol / 12 h / 20 °C / 760.05 Torr

3.1: 1.28 g / H₂; HCl / Pd(OH)2/C / methanol / 2 h / 20 °C / 760.05 Torr

4.1: 61 percent / dimethylformamide / 15 h / 20 °C

5.1: 87 percent / camphorsulfonic acid / acetonitrile / 2 h / 20 °C

6.1: Bu₂SnO / methanol / Heating

6.2: 86 percent / Et₃N / CH₂Cl₂ / 1.5 h / 20 °C

7.1: 74 percent / Ag₂O; 4 Angstroem molecular sieves / CH₂Cl₂ / 48 h / 20 °C

8.1: 99 percent / KOH / methanol / 3 h / 20 °C

9.1: 99 percent / NaH / dimethylformamide / 0 - 20 °C

With hydrogenchloride; potassium hydroxide; 4 A molecular sieve; camphor-10-sulfonic acid; water; hydrogen; sodium hydride; di(n-butyl)tin oxide; silver(l) oxide; palladium dihydroxide; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.tet.2007.04.070

Reference yield:

: 945394-86-5
6-azido-6-deoxy-1-O-benzyl-α-L-sorbofuranose

: 945395-01-7
2-O-allyl-3-O-benzyl-N-(tert-butoxycarbonyl)-1,5-dideoxy-1,5-imino-4,6-O-(4-methoxybenzylidene)-D-glucitol

Guidance literature:: Multi-step reaction with 8 steps

1.1: H₂ / Pd(OH)2/C / methanol / 12 h / 20 °C / 760.05 Torr

2.1: 1.28 g / H₂; HCl / Pd(OH)2/C / methanol / 2 h / 20 °C / 760.05 Torr

3.1: 61 percent / dimethylformamide / 15 h / 20 °C

4.1: 87 percent / camphorsulfonic acid / acetonitrile / 2 h / 20 °C

5.1: Bu₂SnO / methanol / Heating

5.2: 86 percent / Et₃N / CH₂Cl₂ / 1.5 h / 20 °C

6.1: 74 percent / Ag₂O; 4 Angstroem molecular sieves / CH₂Cl₂ / 48 h / 20 °C

7.1: 99 percent / KOH / methanol / 3 h / 20 °C

8.1: 99 percent / NaH / dimethylformamide / 0 - 20 °C

With hydrogenchloride; potassium hydroxide; 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen; sodium hydride; di(n-butyl)tin oxide; silver(l) oxide; palladium dihydroxide; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.tet.2007.04.070