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

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-1-O-(p-methoxybenzyl)-3,4,5-tri-O-benzyl-myo-inositol
CAS No.:475650-99-8
Molecular Formula:C₇₄H₉₃N₃O₁₂
Molecular Weight:1216.57
Hs Code.:

Synonyms: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

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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-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-4-O-(2-propenyl)-α-D-glucopyranosyl]-2-O-hexadecanoyl-1-O-(p-methoxybenzyl)-3,4,5-tri-O-benzyl-myo-inositol

There total 31 articles about 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 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: 40.0%

: 475650-87-4
(2R,3S,4R,5R)-3-Allyloxy-5-azido-4-benzyloxy-2-benzyloxymethyl-6-fluoro-tetrahydro-pyran

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

: 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

Guidance literature:: With bis(cyclopentadienyl)hafnium dichloride; MS 4 Angstroem; silver trifluoromethanesulfonate; In diethyl ether; at -15 - 20 ℃;
DOI:10.1016/S0960-894X(02)00301-3

Reference yield:

: 100-39-0
benzyl bromide

: 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

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: 106 mg / silver triflate; hafnocene dichloride; molecular sieves 4 Angstroem / diethyl ether / -15 - 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

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 9 steps

1.1: Bu₂SnO / toluene / 2.5 h / Heating

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

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

3.1: 60 percent / acetyl chloride / methanol; CH₂Cl₂ / 0.17 h / 20 °C

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

5.1: 0.97 g / acetyl chloride / methanol; CH₂Cl₂ / 2 h / 20 °C

6.1: Bu₂SnO / toluene / 2.5 h / Heating

6.2: 97.5 percent / CsF / 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: 106 mg / silver triflate; hafnocene dichloride; molecular sieves 4 Angstroem / diethyl ether / -15 - 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