Acetic acid (2S,3S,4S,5S)-4-acetoxy-5-{2-acetoxy-4-[(E)-2-((3aS,4R,5S,6S,7R,7aS)-4,6,7-triacetoxy-hexahydro-benzo[1,3]dioxol-5-ylcarbamoyl)-propenyl]-phenoxy}-2-(2-methyl-[1,3]dioxolan-2-yl)-tetrahydro-furan-3-yl ester

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Chemical Name:Acetic acid (2S,3S,4S,5S)-4-acetoxy-5-{2-acetoxy-4-[(E)-2-((3aS,4R,5S,6S,7R,7aS)-4,6,7-triacetoxy-hexahydro-benzo[1,3]dioxol-5-ylcarbamoyl)-propenyl]-phenoxy}-2-(2-methyl-[1,3]dioxolan-2-yl)-tetrahydro-furan-3-yl ester
CAS No.:122777-43-9
Molecular Formula:C₃₇H₄₅NO₁₉
Molecular Weight:807.76
Hs Code.:

Acetic acid (2S,3S,4S,5S)-4-acetoxy-5-{2-acetoxy-4-[(E)-2-((3aS,4R,5S,6S,7R,7aS)-4,6,7-triacetoxy-hexahydro-benzo[1,3]dioxol-5-ylcarbamoyl)-propenyl]-phenoxy}-2-(2-methyl-[1,3]dioxolan-2-yl)-tetrahydro-furan-3-yl ester

Synonyms:Acetic acid (2S,3S,4S,5S)-4-acetoxy-5-{2-acetoxy-4-[(E)-2-((3aS,4R,5S,6S,7R,7aS)-4,6,7-triacetoxy-hexahydro-benzo[1,3]dioxol-5-ylcarbamoyl)-propenyl]-phenoxy}-2-(2-methyl-[1,3]dioxolan-2-yl)-tetrahydro-furan-3-yl ester

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Chemical Property of Acetic acid (2S,3S,4S,5S)-4-acetoxy-5-{2-acetoxy-4-[(E)-2-((3aS,4R,5S,6S,7R,7aS)-4,6,7-triacetoxy-hexahydro-benzo[1,3]dioxol-5-ylcarbamoyl)-propenyl]-phenoxy}-2-(2-methyl-[1,3]dioxolan-2-yl)-tetrahydro-furan-3-yl ester

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Technology Process of Acetic acid (2S,3S,4S,5S)-4-acetoxy-5-{2-acetoxy-4-[(E)-2-((3aS,4R,5S,6S,7R,7aS)-4,6,7-triacetoxy-hexahydro-benzo[1,3]dioxol-5-ylcarbamoyl)-propenyl]-phenoxy}-2-(2-methyl-[1,3]dioxolan-2-yl)-tetrahydro-furan-3-yl ester

There total 14 articles about Acetic acid (2S,3S,4S,5S)-4-acetoxy-5-{2-acetoxy-4-[(E)-2-((3aS,4R,5S,6S,7R,7aS)-4,6,7-triacetoxy-hexahydro-benzo[1,3]dioxol-5-ylcarbamoyl)-propenyl]-phenoxy}-2-(2-methyl-[1,3]dioxolan-2-yl)-tetrahydro-furan-3-yl ester 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:

: 33164-03-3
methyl 2,3-di-O-benzyl-α-D-altropyranoside

: 122777-43-9
Acetic acid (2S,3S,4S,5S)-4-acetoxy-5-{2-acetoxy-4-[(E)-2-((3aS,4R,5S,6S,7R,7aS)-4,6,7-triacetoxy-hexahydro-benzo[1,3]dioxol-5-ylcarbamoyl)-propenyl]-phenoxy}-2-(2-methyl-[1,3]dioxolan-2-yl)-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 74 percent / diethyl azodicarboxylate, triphenylphosphine, CH₃I / tetrahydrofuran / 19 h / Ambient temperature

2: DBU / toluene / 23 h / 80 °C

3: Amberlite IR 120 B resin / tetrahydrofuran; H₂O / 22 h / Ambient temperature

4: 77 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 2.5 h / Ambient temperature

5: 46 percent / H₂ / Pd(OH)2/C / ethyl acetate / 0.5 h / 760 Torr / Ambient temperature

6: 96 percent / pyridine / Ambient temperature

7: 86 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 8 h / -5 °C

8: 66 percent / ceric ammonium nitrate / acetonitrile; H₂O / 14 h / 5 °C

9: 94 percent / CH₂Cl₂ / 14 h / Ambient temperature

10: 1.) 1M aq. NaOH, 2.) pyridine / 1.) MeOH, 50 deg C, overnight, 2.) overnight

11: 1.) diethyl cyanophosphonate, NEt₃, 2.) pyridine / 1.) DMF, 0 deg C, 2.5 h, 2.) RT, 2 h

With pyridine; sodium hydroxide; ammonium cerium(IV) nitrate; diethyl cyanophosphonate; trimethylsilyl trifluoromethanesulfonate; Amberlite IR 120 B resin; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; diethylazodicarboxylate; methyl iodide; palladium dihydroxide; In tetrahydrofuran; dichloromethane; water; ethyl acetate; toluene; acetonitrile;
DOI:10.1021/jo00009a009

Reference yield:

: 118068-40-9
(3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-methoxy-2-methylene-tetrahydro-pyran-3-ol

: 122777-43-9
Acetic acid (2S,3S,4S,5S)-4-acetoxy-5-{2-acetoxy-4-[(E)-2-((3aS,4R,5S,6S,7R,7aS)-4,6,7-triacetoxy-hexahydro-benzo[1,3]dioxol-5-ylcarbamoyl)-propenyl]-phenoxy}-2-(2-methyl-[1,3]dioxolan-2-yl)-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1: Amberlite IR 120 B resin / tetrahydrofuran; H₂O / 22 h / Ambient temperature

2: 77 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 2.5 h / Ambient temperature

3: 46 percent / H₂ / Pd(OH)2/C / ethyl acetate / 0.5 h / 760 Torr / Ambient temperature

4: 96 percent / pyridine / Ambient temperature

5: 86 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 8 h / -5 °C

6: 66 percent / ceric ammonium nitrate / acetonitrile; H₂O / 14 h / 5 °C

7: 94 percent / CH₂Cl₂ / 14 h / Ambient temperature

8: 1.) 1M aq. NaOH, 2.) pyridine / 1.) MeOH, 50 deg C, overnight, 2.) overnight

9: 1.) diethyl cyanophosphonate, NEt₃, 2.) pyridine / 1.) DMF, 0 deg C, 2.5 h, 2.) RT, 2 h

With pyridine; sodium hydroxide; ammonium cerium(IV) nitrate; diethyl cyanophosphonate; trimethylsilyl trifluoromethanesulfonate; Amberlite IR 120 B resin; hydrogen; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium dihydroxide; In tetrahydrofuran; dichloromethane; water; ethyl acetate; acetonitrile;
DOI:10.1021/jo00009a009

Reference yield:

: 118068-39-6
methyl 2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-altropyranoside

: 122777-43-9
Acetic acid (2S,3S,4S,5S)-4-acetoxy-5-{2-acetoxy-4-[(E)-2-((3aS,4R,5S,6S,7R,7aS)-4,6,7-triacetoxy-hexahydro-benzo[1,3]dioxol-5-ylcarbamoyl)-propenyl]-phenoxy}-2-(2-methyl-[1,3]dioxolan-2-yl)-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 10 steps

1: DBU / toluene / 23 h / 80 °C

2: Amberlite IR 120 B resin / tetrahydrofuran; H₂O / 22 h / Ambient temperature

3: 77 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 2.5 h / Ambient temperature

4: 46 percent / H₂ / Pd(OH)2/C / ethyl acetate / 0.5 h / 760 Torr / Ambient temperature

5: 96 percent / pyridine / Ambient temperature

6: 86 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 8 h / -5 °C

7: 66 percent / ceric ammonium nitrate / acetonitrile; H₂O / 14 h / 5 °C

8: 94 percent / CH₂Cl₂ / 14 h / Ambient temperature

9: 1.) 1M aq. NaOH, 2.) pyridine / 1.) MeOH, 50 deg C, overnight, 2.) overnight

10: 1.) diethyl cyanophosphonate, NEt₃, 2.) pyridine / 1.) DMF, 0 deg C, 2.5 h, 2.) RT, 2 h

With pyridine; sodium hydroxide; ammonium cerium(IV) nitrate; diethyl cyanophosphonate; trimethylsilyl trifluoromethanesulfonate; Amberlite IR 120 B resin; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium dihydroxide; In tetrahydrofuran; dichloromethane; water; ethyl acetate; toluene; acetonitrile;
DOI:10.1021/jo00009a009