Acetic acid (2R,3S,4R,5R,6S)-6-allyloxy-3-benzyloxy-4-(3-benzyloxy-decyloxy)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4R,5R,6S)-6-allyloxy-3-benzyloxy-4-(3-benzyloxy-decyloxy)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 137042-23-0
• Molecular Formula: C₃₇H₅₀F₃NO₈
• Molecular Weight: 693.801

Synonyms:Acetic acid (2R,3S,4R,5R,6S)-6-allyloxy-3-benzyloxy-4-(3-benzyloxy-decyloxy)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Acetic acid (2R,3S,4R,5R,6S)-6-allyloxy-3-benzyloxy-4-(3-benzyloxy-decyloxy)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3S,4R,5R,6S)-6-allyloxy-3-benzyloxy-4-(3-benzyloxy-decyloxy)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-ylmethyl ester

There total 4 articles about Acetic acid (2R,3S,4R,5R,6S)-6-allyloxy-3-benzyloxy-4-(3-benzyloxy-decyloxy)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-ylmethyl 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:

(+/-)-3-benzyloxy-1-hydroxydecane (139573-88-9) → Acetic acid (2R,3S,4R,5R,6S)-6-allyloxy-3-benzyloxy-4-(3-benzyloxy-decyloxy)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-ylmethyl ester (137042-23-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

2: 49 percent / NaH / dimethylformamide / 3 h / 20 - 25 °C

3: 99 percent / 80percent AcOH / 0.5 h / 60 °C

4: 87 percent / pyridine / tetrahydrofuran / 1) 30 min, 0 - 5 deg C, 2) 15h, 25 deg C

5: 31 percent / CF₃SO₃H / CH₂Cl₂ / 15 h

With pyridine; trifluorormethanesulfonic acid; sodium hydride; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(91)89007-3

Reference yield:

(+/-)-3-benzyloxy-1-methanesulfonyloxydecane (132792-08-6) → Acetic acid (2R,3S,4R,5R,6S)-6-allyloxy-3-benzyloxy-4-(3-benzyloxy-decyloxy)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-ylmethyl ester (137042-23-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 49 percent / NaH / dimethylformamide / 3 h / 20 - 25 °C

2: 99 percent / 80percent AcOH / 0.5 h / 60 °C

3: 87 percent / pyridine / tetrahydrofuran / 1) 30 min, 0 - 5 deg C, 2) 15h, 25 deg C

4: 31 percent / CF₃SO₃H / CH₂Cl₂ / 15 h

With pyridine; trifluorormethanesulfonic acid; sodium hydride; acetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(91)89007-3

Reference yield:

N-[(2S,3R,4R,5S,6R)-2-Allyloxy-4-(3-benzyloxy-decyloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-2,2,2-trifluoro-acetamide (137042-21-8) → Acetic acid (2R,3S,4R,5R,6S)-6-allyloxy-3-benzyloxy-4-(3-benzyloxy-decyloxy)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-ylmethyl ester (137042-23-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / pyridine / tetrahydrofuran / 1) 30 min, 0 - 5 deg C, 2) 15h, 25 deg C

2: 31 percent / CF₃SO₃H / CH₂Cl₂ / 15 h

With pyridine; trifluorormethanesulfonic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0008-6215(91)89007-3

upstream raw materials:

(+/-)-3-benzyloxy-1-hydroxydecane

(+/-)-3-benzyloxy-1-methanesulfonyloxydecane

N-[(2S,3R,4R,5S,6R)-2-Allyloxy-4-(3-benzyloxy-decyloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-2,2,2-trifluoro-acetamide

N-[(4aR,6S,7R,8R,8aS)-6-Allyloxy-8-(3-benzyloxy-decyloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-2,2,2-trifluoro-acetamide

Downstream raw materials:

allyl 6-O-<(3,4,6-tri-O-acetyl-2-deoxy-2-triflouroacetamido)-β-D-glucopyranosyl>-4-O-benzyl-3-O-<(3RS)-3-(benzyloxy)decanyl>-2-deoxy-2-triflouroacetamido-α-D-glucopyranoside

C₄₆H₆₂F₆N₂O₁₂

N-{(2S,3R,4R,5S,6R)-2-Allyloxy-5-benzyloxy-4-(3-benzyloxy-decyloxy)-6-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-3-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-yloxymethyl]-tetrahydro-pyran-3-yl}-2,2,2-trifluoro-acetamide

allyl 4-O-benzyl-3-O-<(3RS)-3-(benzyloxy)decanyl>-2-deoxy-2-triflouroacetamido-α-D-glucopyranoside

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