Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5S,6S)-6-(2-azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-4-methoxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5S,6S)-6-(2-azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-4-methoxy-tetrahydro-pyran-3-yl ester
• CAS No.: 511511-45-8
• Molecular Formula: C₃₀H₄₃N₃O₁₃
• Molecular Weight: 653.684

Synonyms:Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5S,6S)-6-(2-azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-4-methoxy-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5S,6S)-6-(2-azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-4-methoxy-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5S,6S)-6-(2-azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-4-methoxy-tetrahydro-pyran-3-yl ester

There total 6 articles about Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5S,6S)-6-(2-azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-4-methoxy-tetrahydro-pyran-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: 88.0%

ethyl 2,4,6-tri-O-acetyl-3-O-methyl-1-thio-α/β-L-iodopyranose + (2R,3R,4S,5S,6S)-6-(2-Azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-ol (511511-29-8) → Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5S,6S)-6-(2-azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-4-methoxy-tetrahydro-pyran-3-yl ester (511511-45-8)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In 1,4-dioxane; dichloromethane; toluene; at -20 ℃; for 0.5h;

DOI:10.1002/1099-0690(200212)2002:23<3954::AID-EJOC3954>3.0.CO;2-2

Reference yield:

[(2S,3S,4R,5R,6R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-6-methoxymethyl-tetrahydro-pyran-2-yl]-acetaldehyde → Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5S,6S)-6-(2-azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-4-methoxy-tetrahydro-pyran-3-yl ester (511511-45-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 0.952 g / LiAlH₄ / tetrahydrofuran / 0.5 h

2: pyridine / CH₂Cl₂ / 16 h

3: NaN₃ / dimethylformamide / 3 h / 60 °C

4: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h

5: 88 percent / N-iodosuccinimide; mol. sieves 4 Angstroem; TfOH / toluene; dioxane; CH₂Cl₂ / 0.5 h / -20 °C

With pyridine; N-iodo-succinimide; lithium aluminium tetrahydride; sodium azide; trifluorormethanesulfonic acid; 4 A molecular sieve; tetrabutyl ammonium fluoride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1002/1099-0690(200212)2002:23<3954::AID-EJOC3954>3.0.CO;2-2

Reference yield:

2-[(2S,3S,4R,5R,6R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-6-methoxymethyl-tetrahydro-pyran-2-yl]-ethanol (511511-37-8) → Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5S,6S)-6-(2-azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-4-methoxy-tetrahydro-pyran-3-yl ester (511511-45-8)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / CH₂Cl₂ / 16 h

2: NaN₃ / dimethylformamide / 3 h / 60 °C

3: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h

4: 88 percent / N-iodosuccinimide; mol. sieves 4 Angstroem; TfOH / toluene; dioxane; CH₂Cl₂ / 0.5 h / -20 °C

With pyridine; N-iodo-succinimide; sodium azide; trifluorormethanesulfonic acid; 4 A molecular sieve; tetrabutyl ammonium fluoride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1002/1099-0690(200212)2002:23<3954::AID-EJOC3954>3.0.CO;2-2

upstream raw materials:

(2R,3R,4S,5S,6S)-6-(2-Azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-ol

2-[(2S,3S,4R,5R,6R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-6-methoxymethyl-tetrahydro-pyran-2-yl]-ethanol

((2R,3R,4R,5S,6S)-6-Allyl-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

[(2R,3R,4R,5S,6S)-6-(2-Azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

Downstream raw materials:

(2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6S)-6-(2-Azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-3-hydroxy-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid benzyl ester

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