2'-ethoxy (ethyl 2,4-dideoxy-2-iodo-6-O-p-toluenesulfonyl-α-D-altropyranosido)-<3,4:5',4'>-Δ₂-oxazoline

Base Information

• Chemical Name: 2'-ethoxy (ethyl 2,4-dideoxy-2-iodo-6-O-p-toluenesulfonyl-α-D-altropyranosido)-<3,4:5',4'>-Δ₂-oxazoline
• CAS No.: 92539-82-7
• Molecular Formula: C₁₈H₂₄INO₇S
• Molecular Weight: 525.362

Synonyms:2'-ethoxy (ethyl 2,4-dideoxy-2-iodo-6-O-p-toluenesulfonyl-α-D-altropyranosido)-<3,4:5',4'>-Δ₂-oxazoline

Chemical Property of 2'-ethoxy (ethyl 2,4-dideoxy-2-iodo-6-O-p-toluenesulfonyl-α-D-altropyranosido)-<3,4:5',4'>-Δ₂-oxazoline

Chemical Property:

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Technology Process of 2'-ethoxy (ethyl 2,4-dideoxy-2-iodo-6-O-p-toluenesulfonyl-α-D-altropyranosido)-<3,4:5',4'>-Δ₂-oxazoline

There total 8 articles about 2'-ethoxy (ethyl 2,4-dideoxy-2-iodo-6-O-p-toluenesulfonyl-α-D-altropyranosido)-<3,4:5',4'>-Δ₂-oxazoline 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: 61.0%

ethyl 2,3,4-trideoxy-4-N-ethoxycarbonylamino-6-O-p-toluenesulfonyl-α-D-erythro-hex-2-enopyranoside (92539-81-6) → 2'-ethoxy (ethyl 2,4-dideoxy-2-iodo-6-O-p-toluenesulfonyl-α-D-altropyranosido)-<3,4:5',4'>-Δ2-oxazoline (92539-82-7)

Guidance literature:

With iodonium di(2,4,6-trimethylpyridine) perchlorate; In dichloromethane; at 23 ℃; for 24h; in dark;

DOI:10.1139/v84-262

Reference yield:

ethyl 2,3-dideoxy-α-D-threo-hex-2-enopyranoside (52471-76-8,23339-15-3,56196-33-9,63526-95-4) → 2'-ethoxy (ethyl 2,4-dideoxy-2-iodo-6-O-p-toluenesulfonyl-α-D-altropyranosido)-<3,4:5',4'>-Δ2-oxazoline (92539-82-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 86 percent / pyridine / 48 h / 0 °C

2: 77 percent / sodium azide / dimethylsulfoxide / 0.75 h / 23 °C

3: 90 percent / lithium aluminium hydride / diethyl ether / 0.5 h / -25 °C

4: 86 percent / triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

5: 61 percent / iodonium dicollidine perchlorate / CH₂Cl₂ / 24 h / 23 °C / in dark

With lithium aluminium tetrahydride; sodium azide; iodonium di(2,4,6-trimethylpyridine) perchlorate; triethylamine; In pyridine; diethyl ether; dichloromethane; dimethyl sulfoxide;

DOI:10.1139/v84-262

Reference yield:

ethyl 4,6-di-O-benzoyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside (56932-85-5) → 2'-ethoxy (ethyl 2,4-dideoxy-2-iodo-6-O-p-toluenesulfonyl-α-D-altropyranosido)-<3,4:5',4'>-Δ2-oxazoline (92539-82-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 75 percent / sodium methoxide / methanol / 2 h / 23 °C

2: 86 percent / pyridine / 48 h / 0 °C

3: 77 percent / sodium azide / dimethylsulfoxide / 0.75 h / 23 °C

4: 90 percent / lithium aluminium hydride / diethyl ether / 0.5 h / -25 °C

5: 86 percent / triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

6: 61 percent / iodonium dicollidine perchlorate / CH₂Cl₂ / 24 h / 23 °C / in dark

With lithium aluminium tetrahydride; sodium azide; iodonium di(2,4,6-trimethylpyridine) perchlorate; sodium methylate; triethylamine; In pyridine; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide;

DOI:10.1139/v84-262

upstream raw materials:

ethyl 2,3,4-trideoxy-4-N-ethoxycarbonylamino-6-O-p-toluenesulfonyl-α-D-erythro-hex-2-enopyranoside

ethyl 2,3-dideoxy-α-D-threo-hex-2-enopyranoside

ethyl 4,6-di-O-benzoyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside

ethyl 4-azido-2,3,4-trideoxy-6-O-p-toluenesulfonyl-α-D-erythro-hex-2-enopyranoside

Downstream raw materials:

ethyl 4-N-ethoxycarbonylamino-2,3,4-trideoxy-6-O-p-toluenesulfonyl-α-D-erythro-hexopyranoside

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