1-O-benzyl-6-deoxy-6-iodo-2,3:4,5-bis-O-(1-methylethylidene)-1-(2-thiazolyl)-D-glycero-D-gulo-hexitol

Base Information

Chemical Name:1-O-benzyl-6-deoxy-6-iodo-2,3:4,5-bis-O-(1-methylethylidene)-1-(2-thiazolyl)-D-glycero-D-gulo-hexitol
CAS No.:354137-27-2
Molecular Formula:C₂₂H₂₈INO₅S
Molecular Weight:545.439
Hs Code.:

Synonyms:1-O-benzyl-6-deoxy-6-iodo-2,3:4,5-bis-O-(1-methylethylidene)-1-(2-thiazolyl)-D-glycero-D-gulo-hexitol

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Chemical Property of 1-O-benzyl-6-deoxy-6-iodo-2,3:4,5-bis-O-(1-methylethylidene)-1-(2-thiazolyl)-D-glycero-D-gulo-hexitol

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Technology Process of 1-O-benzyl-6-deoxy-6-iodo-2,3:4,5-bis-O-(1-methylethylidene)-1-(2-thiazolyl)-D-glycero-D-gulo-hexitol

There total 4 articles about 1-O-benzyl-6-deoxy-6-iodo-2,3:4,5-bis-O-(1-methylethylidene)-1-(2-thiazolyl)-D-glycero-D-gulo-hexitol 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: 92.0%

: 100-39-0
benzyl bromide

: 354137-26-1
6-deoxy-6-iodo-2,3:4,5-bis-O-(1-methylethylidene)-1-(2-thiazolyl)-D-glycero-D-gulo-hexitol

: 354137-27-2
1-O-benzyl-6-deoxy-6-iodo-2,3:4,5-bis-O-(1-methylethylidene)-1-(2-thiazolyl)-D-glycero-D-gulo-hexitol

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 20 ℃; for 15h;
DOI:10.1016/S0040-4020(01)00410-0

Reference yield:

: 6207-30-3,72536-03-9
2,3:4,5-di-O-isopropylidene-D-glucose diethyl dithioacetal

: 354137-27-2
1-O-benzyl-6-deoxy-6-iodo-2,3:4,5-bis-O-(1-methylethylidene)-1-(2-thiazolyl)-D-glycero-D-gulo-hexitol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 70 percent / I₂; PPh₃; imidazole / toluene / 0.17 h / Heating

2.1: 75 percent / HgCl₂; HgO; H₂O / acetone / 6 h / Heating

3.1: CH₂Cl₂ / 18 h / 20 °C

3.2: 60 percent / Bu₄NF / tetrahydrofuran

4.1: 92 percent / NaH; tetrabutylammonium iodide / tetrahydrofuran / 15 h / 20 °C

With 1H-imidazole; water; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; triphenylphosphine; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; dichloromethane; acetone; toluene;
DOI:10.1016/S0040-4020(01)00410-0

Reference yield:

: 288589-53-7
6-deoxy-6-iodo-2,3:4,5-bis-O-(1-methylethylidene)-D-glucose

: 354137-27-2
1-O-benzyl-6-deoxy-6-iodo-2,3:4,5-bis-O-(1-methylethylidene)-1-(2-thiazolyl)-D-glycero-D-gulo-hexitol

Guidance literature:: Multi-step reaction with 2 steps

1.1: CH₂Cl₂ / 18 h / 20 °C

1.2: 60 percent / Bu₄NF / tetrahydrofuran

2.1: 92 percent / NaH; tetrabutylammonium iodide / tetrahydrofuran / 15 h / 20 °C

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4020(01)00410-0