1-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-2,3,4,5,6-penta-O-benzyl-D-chiro-inositol

Base Information

Chemical Name:1-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-2,3,4,5,6-penta-O-benzyl-D-chiro-inositol
CAS No.:899438-14-3
Molecular Formula:C₆₈H₆₉N₃O₁₀
Molecular Weight:1088.31
Hs Code.:

Synonyms:1-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-2,3,4,5,6-penta-O-benzyl-D-chiro-inositol

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Chemical Property of 1-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-2,3,4,5,6-penta-O-benzyl-D-chiro-inositol

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Technology Process of 1-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-2,3,4,5,6-penta-O-benzyl-D-chiro-inositol

There total 7 articles about 1-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-2,3,4,5,6-penta-O-benzyl-D-chiro-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: 67.0%

: (2R,3R,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran

: 158340-85-3
1,2,3,4,5-Penta-O-benzyl-D-chiro-inositol

: 899438-14-3
1-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-2,3,4,5,6-penta-O-benzyl-D-chiro-inositol

Guidance literature:: With Phenylselenyl chloride; silver trifluoromethanesulfonate; In toluene; at -42 ℃; for 1.5h;
DOI:10.1016/j.carres.2006.03.031

Reference yield:

: (3R,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-fluoro-tetrahydro-pyran

: 899438-14-3
1-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-2,3,4,5,6-penta-O-benzyl-D-chiro-inositol

Guidance literature:: Multi-step reaction with 2 steps

1: 61.5 mg / SnCl₄ / 1,2-dichloro-ethane / 0.5 h / 0 °C

2: 67 percent / phenylselenium chloride; AgOTf; 4 A MS / toluene / 1.5 h / -42 °C

With Phenylselenyl chloride; silver trifluoromethanesulfonate; tin(IV) chloride; In 1,2-dichloro-ethane; toluene;
DOI:10.1016/j.carres.2006.03.031

Reference yield:

: 898808-36-1
(2S,3S,4S,5R)-2,3,4,5-Tetrakis-benzyloxy-hexane-1,6-diol

: 899438-14-3
1-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-2,3,4,5,6-penta-O-benzyl-D-chiro-inositol

Guidance literature:: Multi-step reaction with 3 steps

1.1: (COCl)2; DMSO; iPr₂EtNH / tetrahydrofuran / 3 h / -78 - 20 °C

1.2: 55 percent / tBuOH; SmI₂ / tetrahydrofuran / 3.5 h / -78 °C

2.1: dibutyltin oxide / benzene / Heating

2.2: 82 percent / TBABr / benzene / 0.25 h / Heating

3.1: 67 percent / phenylselenium chloride; AgOTf; 4 A MS / toluene / 1.5 h / -42 °C

With Phenylselenyl chloride; oxalyl dichloride; silver trifluoromethanesulfonate; di(n-butyl)tin oxide; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; toluene; benzene; 1.1: Swern oxidation;
DOI:10.1016/j.carres.2006.03.031