Acetic acid (2R,3S,4S,5S,6S)-3-acetoxy-2-acetoxymethyl-6-((2S,3S,4R)-2-azido-3,4-bis-benzyloxy-octadecyloxy)-5-iodo-tetrahydro-pyran-4-yl ester

Base Information

Chemical Name:Acetic acid (2R,3S,4S,5S,6S)-3-acetoxy-2-acetoxymethyl-6-((2S,3S,4R)-2-azido-3,4-bis-benzyloxy-octadecyloxy)-5-iodo-tetrahydro-pyran-4-yl ester
CAS No.:412031-51-7
Molecular Formula:C₄₄H₆₄IN₃O₁₀
Molecular Weight:921.911
Hs Code.:

Synonyms:Acetic acid (2R,3S,4S,5S,6S)-3-acetoxy-2-acetoxymethyl-6-((2S,3S,4R)-2-azido-3,4-bis-benzyloxy-octadecyloxy)-5-iodo-tetrahydro-pyran-4-yl ester

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Chemical Property of Acetic acid (2R,3S,4S,5S,6S)-3-acetoxy-2-acetoxymethyl-6-((2S,3S,4R)-2-azido-3,4-bis-benzyloxy-octadecyloxy)-5-iodo-tetrahydro-pyran-4-yl ester

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Technology Process of Acetic acid (2R,3S,4S,5S,6S)-3-acetoxy-2-acetoxymethyl-6-((2S,3S,4R)-2-azido-3,4-bis-benzyloxy-octadecyloxy)-5-iodo-tetrahydro-pyran-4-yl ester

There total 5 articles about Acetic acid (2R,3S,4S,5S,6S)-3-acetoxy-2-acetoxymethyl-6-((2S,3S,4R)-2-azido-3,4-bis-benzyloxy-octadecyloxy)-5-iodo-tetrahydro-pyran-4-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:

: (2R,3S,4R)-1-O-(triisopropylsilyl)-3,4-di-O-benzyl-6-octadecene-1,2,3,4-tetrol

: 412031-51-7
Acetic acid (2R,3S,4S,5S,6S)-3-acetoxy-2-acetoxymethyl-6-((2S,3S,4R)-2-azido-3,4-bis-benzyloxy-octadecyloxy)-5-iodo-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 85 percent / TsNHNH₂; AcONa / aq. ethanol / 5 h / Heating

2: pyridine / CH₂Cl₂ / 0.5 h / -15 °C

3: 1.04 g / NaN₃ / CH₂Cl₂; dimethylformamide; pyridine / 12 h / 20 °C

4: 82 percent / TBAF / tetrahydrofuran / 1.67 h / 0 - 20 °C

5: N-iodosuccinmimide / CH₂Cl₂ / 1.5 h / Heating

With pyridine; N-iodo-succinimide; sodium azide; tetrabutyl ammonium fluoride; sodium acetate; toluene-4-sulfonic acid hydrazide; In tetrahydrofuran; pyridine; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)01163-2

Reference yield:

: 412031-49-3
(2R,3S,4R)-3,4-Bis-benzyloxy-1-triisopropylsilanyloxy-octadecan-2-ol

: 412031-51-7
Acetic acid (2R,3S,4S,5S,6S)-3-acetoxy-2-acetoxymethyl-6-((2S,3S,4R)-2-azido-3,4-bis-benzyloxy-octadecyloxy)-5-iodo-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: pyridine / CH₂Cl₂ / 0.5 h / -15 °C

2: 1.04 g / NaN₃ / CH₂Cl₂; dimethylformamide; pyridine / 12 h / 20 °C

3: 82 percent / TBAF / tetrahydrofuran / 1.67 h / 0 - 20 °C

4: N-iodosuccinmimide / CH₂Cl₂ / 1.5 h / Heating

With pyridine; N-iodo-succinimide; sodium azide; tetrabutyl ammonium fluoride; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)01163-2

Reference yield:

: 412031-50-6
((2S,3S,4R)-2-Azido-3,4-bis-benzyloxy-octadecyloxy)-triisopropyl-silane

: 412031-51-7
Acetic acid (2R,3S,4S,5S,6S)-3-acetoxy-2-acetoxymethyl-6-((2S,3S,4R)-2-azido-3,4-bis-benzyloxy-octadecyloxy)-5-iodo-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 82 percent / TBAF / tetrahydrofuran / 1.67 h / 0 - 20 °C

2: N-iodosuccinmimide / CH₂Cl₂ / 1.5 h / Heating

With N-iodo-succinimide; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4020(01)01163-2