6-O-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-O-hexadecanoyl-1-O-(p-methoxybenzyl)-3,4,5-tri-O-benzyl-myo-inositol

Base Information

Chemical Name:6-O-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-O-hexadecanoyl-1-O-(p-methoxybenzyl)-3,4,5-tri-O-benzyl-myo-inositol
CAS No.:543698-59-5
Molecular Formula:C₇₁H₈₉N₃O₁₂
Molecular Weight:1176.5
Hs Code.:

Synonyms:6-O-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-O-hexadecanoyl-1-O-(p-methoxybenzyl)-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-α-D-glucopyranosyl)-2-O-hexadecanoyl-1-O-(p-methoxybenzyl)-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-α-D-glucopyranosyl)-2-O-hexadecanoyl-1-O-(p-methoxybenzyl)-3,4,5-tri-O-benzyl-myo-inositol

There total 27 articles about 6-O-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-O-hexadecanoyl-1-O-(p-methoxybenzyl)-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: 84.0%

: 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

: 543698-59-5
6-O-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-O-hexadecanoyl-1-O-(p-methoxybenzyl)-3,4,5-tri-O-benzyl-myo-inositol

Guidance literature:: With palladium dichloride;
DOI:10.1021/ja0382157

Reference yield:

: 100-39-0
benzyl bromide

: 475650-96-5
4-O-allyl-2-azido-3-O-benzyl-2-deoxy-D-glucopyranosyl fluoride

: 475650-88-5
(-)-2-O-hexadecanoyl-1-O-(p-methoxybenzyl)-3,4,5-tri-O-benzyl-myo-inositol

: 6-O-(2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-2-O-hexadecanoyl-1-O-(p-methoxybenzyl)-3,4,5-tri-O-benzyl-myo-inositol

: 543698-59-5
6-O-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-O-hexadecanoyl-1-O-(p-methoxybenzyl)-3,4,5-tri-O-benzyl-myo-inositol

Guidance literature:: benzyl bromide; 4-O-allyl-2-azido-3-O-benzyl-2-deoxy-D-glucopyranosyl fluoride; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

(-)-2-O-hexadecanoyl-1-O-(p-methoxybenzyl)-3,4,5-tri-O-benzyl-myo-inositol; With bis(cyclopentadienyl)hafnium dichloride; 4 A molecular sieve; silver trifluoromethanesulfonate; In diethyl ether; at -15 - 20 ℃;

With sodium acetate; acetic acid; palladium dichloride; In water; at 20 ℃; for 18h;
DOI:10.1021/jo034213t

Reference yield:

: 100-39-0
benzyl bromide

: 543698-59-5
6-O-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-O-hexadecanoyl-1-O-(p-methoxybenzyl)-3,4,5-tri-O-benzyl-myo-inositol

Guidance literature:: Multi-step reaction with 9 steps

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

2.1: 1.98 g / acetyl chloride / methanol; CH₂Cl₂ / 0.17 h / 20 °C

3.1: Bu₂SnO / toluene / 2.5 h / Heating

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

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

5.1: 1.37 g / acetyl chloride / methanol; CH₂Cl₂ / 2 h / 20 °C

6.1: Bu₂SnO / toluene / 2.5 h / Heating

6.2: 94 percent / CsF; NaI / dimethylformamide / 17 h / -10 - 20 °C

7.1: 2.2 g / DMAP; DCC / CH₂Cl₂ / 24 h / 20 °C

8.1: 94 percent / acetic acid; NaOAc / PdCl₂ / H₂O / 18 h / 20 °C

9.1: NaH / dimethylformamide / 3 h / 20 °C

9.2: silver triflate; hafnocene dichloride; molecular sieves 4 Angstroem / diethyl ether / -15 - 20 °C

9.3: 0.53 g / acetic acid; NaOAc / PdCl₂ / H₂O / 18 h / 20 °C

With dmap; sodium acetate; sodium hydride; di(n-butyl)tin oxide; acetic acid; acetyl chloride; dicyclohexyl-carbodiimide; palladium dichloride; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo034213t