O-(3,4,6-tri-O-benzyl-2-O-<(pentafluorophenoxy)thiocarbonyl>-β-D-glucosyl)-(1<*>3)-1,5-anhydro-4,6-di-O-benzyl-2-deoxy-D-lyxo-hex-1-enopyranose

Base Information

Chemical Name:O-(3,4,6-tri-O-benzyl-2-O-<(pentafluorophenoxy)thiocarbonyl>-β-D-glucosyl)-(1<*>3)-1,5-anhydro-4,6-di-O-benzyl-2-deoxy-D-lyxo-hex-1-enopyranose
CAS No.:135192-36-8
Molecular Formula:C₅₄H₄₉F₅O₁₀S
Molecular Weight:985.035
Hs Code.:

Synonyms:O-(3,4,6-tri-O-benzyl-2-O-<(pentafluorophenoxy)thiocarbonyl>-β-D-glucosyl)-(1<*>3)-1,5-anhydro-4,6-di-O-benzyl-2-deoxy-D-lyxo-hex-1-enopyranose

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Chemical Property of O-(3,4,6-tri-O-benzyl-2-O-<(pentafluorophenoxy)thiocarbonyl>-β-D-glucosyl)-(1<*>3)-1,5-anhydro-4,6-di-O-benzyl-2-deoxy-D-lyxo-hex-1-enopyranose

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Technology Process of O-(3,4,6-tri-O-benzyl-2-O-<(pentafluorophenoxy)thiocarbonyl>-β-D-glucosyl)-(1<*>3)-1,5-anhydro-4,6-di-O-benzyl-2-deoxy-D-lyxo-hex-1-enopyranose

There total 3 articles about O-(3,4,6-tri-O-benzyl-2-O-<(pentafluorophenoxy)thiocarbonyl>-β-D-glucosyl)-(1<*>3)-1,5-anhydro-4,6-di-O-benzyl-2-deoxy-D-lyxo-hex-1-enopyranose 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: 73.0%

: 135192-53-9
pentafluorophenoxythiocarbonyl chloride

: 135192-33-5
O-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1<*>3)-1,5-anhydro-4,6-di-O-benzyl-2-deoxy-D-lyxo-hex-1-enitol

: 135192-36-8
O-(3,4,6-tri-O-benzyl-2-O-<(pentafluorophenoxy)thiocarbonyl>-β-D-glucosyl)-(1<*>3)-1,5-anhydro-4,6-di-O-benzyl-2-deoxy-D-lyxo-hex-1-enopyranose

Guidance literature:: With pyridine; 1-hydroxy-pyrrolidine-2,5-dione; In toluene; at 80 ℃; for 4h;
DOI:10.1021/jo00018a047

Reference yield:

: 55628-54-1
3,4,6-tri-O-benzyl-D-glucal

: 135192-36-8
O-(3,4,6-tri-O-benzyl-2-O-<(pentafluorophenoxy)thiocarbonyl>-β-D-glucosyl)-(1<*>3)-1,5-anhydro-4,6-di-O-benzyl-2-deoxy-D-lyxo-hex-1-enopyranose

Guidance literature:: Multi-step reaction with 3 steps

1: 3,3-dimethyldioxirane / CH₂Cl₂ / 0.25 h / 0 °C

2: ZnCl₂ / tetrahydrofuran; diethyl ether / 1.) -78 deg C to 25 deg C, 2.) 25 deg C, overnight

3: 73 percent / N-hydroxysuccinimide, pyridine / toluene / 4 h / 80 °C

With pyridine; 1-hydroxy-pyrrolidine-2,5-dione; 3,3-dimethyldioxirane; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/jo00018a047

Reference yield:

: 74372-90-0
3,4,6-tri-O-benzyl-D-glucal epoxide

: 135192-36-8
O-(3,4,6-tri-O-benzyl-2-O-<(pentafluorophenoxy)thiocarbonyl>-β-D-glucosyl)-(1<*>3)-1,5-anhydro-4,6-di-O-benzyl-2-deoxy-D-lyxo-hex-1-enopyranose

Guidance literature:: Multi-step reaction with 2 steps

1: ZnCl₂ / tetrahydrofuran; diethyl ether / 1.) -78 deg C to 25 deg C, 2.) 25 deg C, overnight

2: 73 percent / N-hydroxysuccinimide, pyridine / toluene / 4 h / 80 °C

With pyridine; 1-hydroxy-pyrrolidine-2,5-dione; zinc(II) chloride; In tetrahydrofuran; diethyl ether; toluene;
DOI:10.1021/jo00018a047