6-O-[2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(2-propenyl)-α-D-glucopyranosyl]-2-O-hexadecanoyl-3,4,5-tri-O-benzyl-myo-inositol

Base Information

Chemical Name:6-O-[2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(2-propenyl)-α-D-glucopyranosyl]-2-O-hexadecanoyl-3,4,5-tri-O-benzyl-myo-inositol
CAS No.:475651-00-4
Molecular Formula:C₆₆H₈₅N₃O₁₁
Molecular Weight:1096.41
Hs Code.:

Synonyms:6-O-[2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(2-propenyl)-α-D-glucopyranosyl]-2-O-hexadecanoyl-3,4,5-tri-O-benzyl-myo-inositol

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Chemical Property of 6-O-[2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(2-propenyl)-α-D-glucopyranosyl]-2-O-hexadecanoyl-3,4,5-tri-O-benzyl-myo-inositol

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Technology Process of 6-O-[2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(2-propenyl)-α-D-glucopyranosyl]-2-O-hexadecanoyl-3,4,5-tri-O-benzyl-myo-inositol

There total 23 articles about 6-O-[2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(2-propenyl)-α-D-glucopyranosyl]-2-O-hexadecanoyl-3,4,5-tri-O-benzyl-myo-inositol 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: 80.0%

: 475650-99-8
6-O-[2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(2-propenyl)-α-D-glucopyranosyl]-2-O-hexadecanoyl-1-O-(p-methoxybenzyl)-3,4,5-tri-O-benzyl-myo-inositol

: 475651-00-4
6-O-[2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(2-propenyl)-α-D-glucopyranosyl]-2-O-hexadecanoyl-3,4,5-tri-O-benzyl-myo-inositol

Guidance literature:: With ammonium cerium(IV) nitrate; In water; acetonitrile; at 20 ℃; for 2h;
DOI:10.1016/S0960-894X(02)00301-3

Reference yield:

: 41545-19-1
(+)-1,2:5,6-di-O-cyclohexylidene-myo-inositol

: 475651-00-4
6-O-[2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(2-propenyl)-α-D-glucopyranosyl]-2-O-hexadecanoyl-3,4,5-tri-O-benzyl-myo-inositol

Guidance literature:: Multi-step reaction with 10 steps

1.1: Bu₂SnO / toluene / 2.5 h / Heating

1.2: 80 percent / dimethylformamide / 16 h / 20 °C

2.1: 85 percent / NaH / dimethylformamide / 3 h / 20 °C

3.1: 60 percent / AcCl; MeOH / CH₂Cl₂ / 0.17 h / 20 °C

4.1: 100 percent / NaH / dimethylformamide / 3 h / 20 °C

5.1: 78 percent / AcCl; MeOH / CH₂Cl₂ / 2 h / 20 °C

6.1: Bu₂SnO / toluene / 2.5 h / Heating

6.2: 98 percent / dimethylformamide / 15 h / 20 °C

7.1: 100 percent / DCC; DMAP / CH₂Cl₂ / 20 °C

8.1: 94 percent / PdCl₂; NaOAc; AcOH / tetrahydrofuran / 18 h / 20 °C

9.1: 40 percent / dichlorohafnocene; AgOTf; MS 4 Angstroem / diethyl ether / -15 - 20 °C

10.1: 80 percent / CAN / H₂O; acetonitrile / 2 h / 20 °C

With methanol; dmap; bis(cyclopentadienyl)hafnium dichloride; ammonium cerium(IV) nitrate; MS 4 Angstroem; sodium acetate; silver trifluoromethanesulfonate; sodium hydride; di(n-butyl)tin oxide; acetic acid; acetyl chloride; dicyclohexyl-carbodiimide; palladium dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0960-894X(02)00301-3

Reference yield:

: 33021-17-9
(-)-2,3:4,5-di-O-cyclohexylidene-myo-inositol

: 475651-00-4
6-O-[2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(2-propenyl)-α-D-glucopyranosyl]-2-O-hexadecanoyl-3,4,5-tri-O-benzyl-myo-inositol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 100 percent / NaH / dimethylformamide / 3 h / 20 °C

2.1: 68 percent / AcCl; MeOH / CH₂Cl₂ / 0.17 h / 20 °C

3.1: Bu₂SnO / toluene / 2.5 h / Heating

3.2: 71 percent / dimethylformamide / 16 h / 20 °C

4.1: 100 percent / NaH / dimethylformamide / 3 h / 20 °C

5.1: 89 percent / AcCl; MeOH / CH₂Cl₂ / 2 h / 20 °C

6.1: Bu₂SnO / toluene / 2.5 h / Heating

6.2: 94 percent / dimethylformamide / 16 h / 20 °C

7.1: 100 percent / DCC; DMAP / CH₂Cl₂ / 20 °C

8.1: 94 percent / PdCl₂; NaOAc; AcOH / tetrahydrofuran / 18 h / 20 °C

9.1: 40 percent / dichlorohafnocene; AgOTf; MS 4 Angstroem / diethyl ether / -15 - 20 °C

10.1: 80 percent / CAN / H₂O; acetonitrile / 2 h / 20 °C

With methanol; dmap; bis(cyclopentadienyl)hafnium dichloride; ammonium cerium(IV) nitrate; MS 4 Angstroem; sodium acetate; silver trifluoromethanesulfonate; sodium hydride; di(n-butyl)tin oxide; acetic acid; acetyl chloride; dicyclohexyl-carbodiimide; palladium dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0960-894X(02)00301-3