(4S,5S,13S,14S)-19-benzyloxy-4,5,13,14-tetrabutoxymethyl-3,6,9,12,15-pentaoxa-21-azabicyclo-[15.3.1]heneicosa-1⁽²¹⁾,17,19-triene

Base Information

• Chemical Name: (4S,5S,13S,14S)-19-benzyloxy-4,5,13,14-tetrabutoxymethyl-3,6,9,12,15-pentaoxa-21-azabicyclo-[15.3.1]heneicosa-1⁽²¹⁾,17,19-triene
• CAS No.: 623948-01-6
• Molecular Formula: C₄₂H₆₉NO₁₀
• Molecular Weight: 748.011

Synonyms:(4S,5S,13S,14S)-19-benzyloxy-4,5,13,14-tetrabutoxymethyl-3,6,9,12,15-pentaoxa-21-azabicyclo-[15.3.1]heneicosa-1⁽²¹⁾,17,19-triene

Chemical Property of (4S,5S,13S,14S)-19-benzyloxy-4,5,13,14-tetrabutoxymethyl-3,6,9,12,15-pentaoxa-21-azabicyclo-[15.3.1]heneicosa-1⁽²¹⁾,17,19-triene

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Technology Process of (4S,5S,13S,14S)-19-benzyloxy-4,5,13,14-tetrabutoxymethyl-3,6,9,12,15-pentaoxa-21-azabicyclo-[15.3.1]heneicosa-1⁽²¹⁾,17,19-triene

There total 4 articles about (4S,5S,13S,14S)-19-benzyloxy-4,5,13,14-tetrabutoxymethyl-3,6,9,12,15-pentaoxa-21-azabicyclo-[15.3.1]heneicosa-1⁽²¹⁾,17,19-triene 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: 64.0%

4-benzyloxy-2,6-pyridinedimethanol ditosylate (249296-17-1) + (7S,8S,16S,17S)-8,16-bis(butoxymethyl)-5,9,12,15,19-pentaoxatricosan-7,17-diol (623948-09-4) → (4S,5S,13S,14S)-19-benzyloxy-4,5,13,14-tetrabutoxymethyl-3,6,9,12,15-pentaoxa-21-azabicyclo-[15.3.1]heneicosa-1(21),17,19-triene (623948-01-6)

Guidance literature:

(7S,8S,16S,17S)-8,16-bis(butoxymethyl)-5,9,12,15,19-pentaoxatricosan-7,17-diol; With sodium hydride; In tetrahydrofuran; at 0 - 50 ℃;

4-benzyloxy-2,6-pyridinedimethanol ditosylate; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/S0957-4166(03)00590-1

Reference yield:

(S,S)-1,4-O,O'-dibutyl-2-O-benzylthreitol (623948-17-4) → (4S,5S,13S,14S)-19-benzyloxy-4,5,13,14-tetrabutoxymethyl-3,6,9,12,15-pentaoxa-21-azabicyclo-[15.3.1]heneicosa-1(21),17,19-triene (623948-01-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 1.25 h / 0 - 50 °C

1.2: tetrahydrofuran / 0 - 60 °C

2.1: 2.5 g / H₂ / Pd/C / ethanol

3.1: NaH / tetrahydrofuran / 0 - 50 °C

3.2: 64 percent / tetrahydrofuran / -78 - 20 °C

With hydrogen; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; ethanol;

DOI:10.1016/S0957-4166(03)00590-1

Reference yield:

(S,S)-2-phenyl-4,5-bis(butoxymethyl)-1,3-dioxolane (623948-16-3) → (4S,5S,13S,14S)-19-benzyloxy-4,5,13,14-tetrabutoxymethyl-3,6,9,12,15-pentaoxa-21-azabicyclo-[15.3.1]heneicosa-1(21),17,19-triene (623948-01-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 83 percent / DIBALH / CH₂Cl₂; toluene / 24 h / 20 °C

2.1: NaH / tetrahydrofuran / 1.25 h / 0 - 50 °C

2.2: tetrahydrofuran / 0 - 60 °C

3.1: 2.5 g / H₂ / Pd/C / ethanol

4.1: NaH / tetrahydrofuran / 0 - 50 °C

4.2: 64 percent / tetrahydrofuran / -78 - 20 °C

With hydrogen; sodium hydride; diisobutylaluminium hydride; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; toluene;

DOI:10.1016/S0957-4166(03)00590-1

upstream raw materials:

4-benzyloxy-2,6-pyridinedimethanol ditosylate

(7S,8S,16S,17S)-8,16-bis(butoxymethyl)-5,9,12,15,19-pentaoxatricosan-7,17-diol

(S,S)-2-phenyl-4,5-bis(butoxymethyl)-1,3-dioxolane

(S,S)-1,4-O,O'-dibutyl-2-O-benzylthreitol

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