3-(2-phenyl-benzo[b]thiophen-3-yl)-prop-2-ynyl 4-azido-2,3,4,6-tetradeoxy-α-L-erythro-hexopyranoside

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Chemical Name:3-(2-phenyl-benzo[b]thiophen-3-yl)-prop-2-ynyl 4-azido-2,3,4,6-tetradeoxy-α-L-erythro-hexopyranoside
CAS No.:1271925-54-2
Molecular Formula:C₂₃H₂₁N₃O₂S
Molecular Weight:403.505
Hs Code.:

Synonyms:3-(2-phenyl-benzo[b]thiophen-3-yl)-prop-2-ynyl 4-azido-2,3,4,6-tetradeoxy-α-L-erythro-hexopyranoside

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Chemical Property of 3-(2-phenyl-benzo[b]thiophen-3-yl)-prop-2-ynyl 4-azido-2,3,4,6-tetradeoxy-α-L-erythro-hexopyranoside

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Technology Process of 3-(2-phenyl-benzo[b]thiophen-3-yl)-prop-2-ynyl 4-azido-2,3,4,6-tetradeoxy-α-L-erythro-hexopyranoside

There total 7 articles about 3-(2-phenyl-benzo[b]thiophen-3-yl)-prop-2-ynyl 4-azido-2,3,4,6-tetradeoxy-α-L-erythro-hexopyranoside 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: 56.0%

: 1271925-53-1
3-(2-phenyl-benzo[b]thiophen-3-yl)-prop-2-ynyl 2,3,6-trideoxy-α-L-threo-hexopyranoside

: 1271925-54-2
3-(2-phenyl-benzo[b]thiophen-3-yl)-prop-2-ynyl 4-azido-2,3,4,6-tetradeoxy-α-L-erythro-hexopyranoside

Guidance literature:: With di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine; In tetrahydrofuran; at -20 - 20 ℃; for 12h;
DOI:10.1016/j.bmc.2011.01.014

Reference yield:

: 1271934-24-7
3-(2-phenyl-benzo[b]thiophen-3-yl)-propyl 2,3,6-trideoxy-α-L-erythro-hexopyranoside

: 1271925-54-2
3-(2-phenyl-benzo[b]thiophen-3-yl)-prop-2-ynyl 4-azido-2,3,4,6-tetradeoxy-α-L-erythro-hexopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine / tetrahydrofuran / 12 h / -20 - 20 °C

2: water; triphenylphosphine / tetrahydrofuran / 10 h / Reflux

3: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 12 h / -20 - 20 °C

4: methanol; sodium methylate / 12 h

5: di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine / tetrahydrofuran / 12 h / -20 - 20 °C

With methanol; di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; water; sodium methylate; triphenylphosphine; In tetrahydrofuran; 1: Mitsunobu reaction / 2: Staudinger reaction / 3: Mitsunobu reaction / 5: Mitsunobu reaction;
DOI:10.1016/j.bmc.2011.01.014

Reference yield:

: 1192235-33-8
3-(2-phenyl-benzo[b]thiophen-3-yl)-prop-2-ynyl 4-O-acetyl-2,3,6-trideoxy-α-L-erythro-hexopyranoside

: 1271925-54-2
3-(2-phenyl-benzo[b]thiophen-3-yl)-prop-2-ynyl 4-azido-2,3,4,6-tetradeoxy-α-L-erythro-hexopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 20 °C / 760.05 Torr

2: methanol; potassium carbonate / 12 h / 20 °C

3: di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine / tetrahydrofuran / 12 h / -20 - 20 °C

4: water; triphenylphosphine / tetrahydrofuran / 10 h / Reflux

5: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 12 h / -20 - 20 °C

6: methanol; sodium methylate / 12 h

7: di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine / tetrahydrofuran / 12 h / -20 - 20 °C

With methanol; di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; palladium 10% on activated carbon; water; hydrogen; sodium methylate; potassium carbonate; triphenylphosphine; In tetrahydrofuran; ethyl acetate; 3: Mitsunobu reaction / 4: Staudinger reaction / 5: Mitsunobu reaction / 7: Mitsunobu reaction;
DOI:10.1016/j.bmc.2011.01.014