((2R,3R,4R,5S,6R)-1-benzyl-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-hydroxypiperidin-6-yl)methyl acetate

Base Information

Chemical Name:((2R,3R,4R,5S,6R)-1-benzyl-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-hydroxypiperidin-6-yl)methyl acetate
CAS No.:1417906-38-7
Molecular Formula:C₃₇H₄₁NO₆
Molecular Weight:595.736
Hs Code.:

Synonyms:((2R,3R,4R,5S,6R)-1-benzyl-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-hydroxypiperidin-6-yl)methyl acetate

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Chemical Property of ((2R,3R,4R,5S,6R)-1-benzyl-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-hydroxypiperidin-6-yl)methyl acetate

Chemical Property:

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Technology Process of ((2R,3R,4R,5S,6R)-1-benzyl-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-hydroxypiperidin-6-yl)methyl acetate

There total 11 articles about ((2R,3R,4R,5S,6R)-1-benzyl-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-hydroxypiperidin-6-yl)methyl acetate 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: 50.0%

: 943135-47-5
(2R,3R,4R,5S,6S)-N-[(tert-butyloxy)carbonyl]-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-5,6-dihydroxyazepane

: 64-19-7,77671-22-8
acetic acid

: 1417906-38-7
((2R,3R,4R,5S,6R)-1-benzyl-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-hydroxypiperidin-6-yl)methyl acetate

: (2R,3R,4R,5S,6S)-N-benzyl-6-acetoxy-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-5-hydroxyazepane

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1021/ol502926f

Reference yield:

: 102208-53-7
(3R,4R,5R)-5-hydroxy-3,4,6-tribenzyloxy-1-hexene

: 1417906-38-7
((2R,3R,4R,5S,6R)-1-benzyl-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-hydroxypiperidin-6-yl)methyl acetate

: (2R,3R,4R,5S,6S)-N-benzyl-6-acetoxy-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-5-hydroxyazepane

Guidance literature:: Multi-step reaction with 10 steps

1.1: diethylazodicarboxylate; triphenylphosphine / toluene / 12 h / 20 °C

2.1: sodium / methanol / 2 h / 20 °C

3.1: pyridine / dichloromethane / 3 h / -20 °C

4.1: triethylamine / dichloromethane / 48.33 h / 20 °C / Molecular sieve

5.1: aminosulfonic acid / dichloromethane / 2 h

5.2: 2 h

6.1: Grubbs catalyst first generation / 1,2-dichloro-ethane / 16 h / 90 °C / Inert atmosphere

6.2: 16 h / 90 °C

7.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / acetone; water; tert-butyl alcohol / 12 h / 20 °C

8.1: dichloromethane / 12 h / 20 °C

9.1: trifluoroacetic acid; triethylsilane / dichloromethane / 2 h / 20 °C

9.2: 18 h / 90 °C

10.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran / 1 h / 0 °C

With pyridine; Grubbs catalyst first generation; triethylsilane; osmium(VIII) oxide; aminosulfonic acid; sodium; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; acetone; toluene; tert-butyl alcohol; 1.1: |Mitsunobu Displacement;
DOI:10.1021/ol502926f

Reference yield:

: (2S,3S,4R)-1,3,4-tris(benzyloxy)hex-5-en-2-yl 4-nitrobenzoate

: 1417906-38-7
((2R,3R,4R,5S,6R)-1-benzyl-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-hydroxypiperidin-6-yl)methyl acetate

: (2R,3R,4R,5S,6S)-N-benzyl-6-acetoxy-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-5-hydroxyazepane

Guidance literature:: Multi-step reaction with 9 steps

1.1: sodium / methanol / 2 h / 20 °C

2.1: pyridine / dichloromethane / 3 h / -20 °C

3.1: triethylamine / dichloromethane / 48.33 h / 20 °C / Molecular sieve

4.1: aminosulfonic acid / dichloromethane / 2 h

4.2: 2 h

5.1: Grubbs catalyst first generation / 1,2-dichloro-ethane / 16 h / 90 °C / Inert atmosphere

5.2: 16 h / 90 °C

6.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / acetone; water; tert-butyl alcohol / 12 h / 20 °C

7.1: dichloromethane / 12 h / 20 °C

8.1: trifluoroacetic acid; triethylsilane / dichloromethane / 2 h / 20 °C

8.2: 18 h / 90 °C

9.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran / 1 h / 0 °C

With pyridine; Grubbs catalyst first generation; triethylsilane; osmium(VIII) oxide; aminosulfonic acid; sodium; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; acetone; tert-butyl alcohol;
DOI:10.1021/ol502926f