Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-[acetyl-(2,2,2-trichloro-ethoxycarbonyl)-amino]-6-((2S,3S,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-[acetyl-(2,2,2-trichloro-ethoxycarbonyl)-amino]-6-((2S,3S,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester
• CAS No.: 187456-09-3
• Molecular Formula: C₄₇H₅₄Cl₃NO₁₆
• Molecular Weight: 995.302
• Mol file: 187456-09-3.mol

Synonyms:

Chemical Property of Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-[acetyl-(2,2,2-trichloro-ethoxycarbonyl)-amino]-6-((2S,3S,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-[acetyl-(2,2,2-trichloro-ethoxycarbonyl)-amino]-6-((2S,3S,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester

There total 6 articles about Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-[acetyl-(2,2,2-trichloro-ethoxycarbonyl)-amino]-6-((2S,3S,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-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: 54.0%

(2S,3S,4R,5R,6R)-2-Allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol (97576-68-6) + Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-[acetyl-(2,2,2-trichloro-ethoxycarbonyl)-amino]-6-ethylsulfanyl-tetrahydro-pyran-4-yl ester (187455-96-5) → Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-[acetyl-(2,2,2-trichloro-ethoxycarbonyl)-amino]-6-((2S,3S,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester (187456-09-3)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1016/S0008-6215(96)00237-6

Reference yield:

(3R,4R,5S,6R)-6-(acetoxymethyl)-3-aminotetrahydro-2H-pyran-2,4,5-triyl triacetate (59042-16-9) → Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-[acetyl-(2,2,2-trichloro-ethoxycarbonyl)-amino]-6-((2S,3S,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester (187456-09-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / EtN(i-Pr)2

2: 92 percent / BF₃*Et₂O / CH₂Cl₂

3: 93 percent / DMP, EtN(iPr)2 / CH₂Cl₂ / 72 h / Ambient temperature

4: 54 percent / TfOH, NIS / CH₂Cl₂ / 2 h / Ambient temperature

With N-iodo-succinimide; trifluorormethanesulfonic acid; phthalic acid dimethyl ester; boron trifluoride diethyl etherate; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1016/S0008-6215(96)00237-6

Reference yield:

(+)-D-glucosamine hydrochloride (1078691-95-8) → Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-[acetyl-(2,2,2-trichloro-ethoxycarbonyl)-amino]-6-((2S,3S,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester (187456-09-3)

Guidance literature:

Multi-step reaction with 5 steps

1: NaHCO₃ / H₂O / 1 h

2: pyridine / Ambient temperature

3: 92 percent / BF₃*Et₂O / CH₂Cl₂

4: 93 percent / DMP, EtN(iPr)2 / CH₂Cl₂ / 72 h / Ambient temperature

5: 54 percent / TfOH, NIS / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; phthalic acid dimethyl ester; boron trifluoride diethyl etherate; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; water;

DOI:10.1016/S0008-6215(96)00237-6

upstream raw materials:

(2S,3S,4R,5R,6R)-2-Allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol

Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-[acetyl-(2,2,2-trichloro-ethoxycarbonyl)-amino]-6-ethylsulfanyl-tetrahydro-pyran-4-yl ester

(3R,4R,5S,6R)-6-(acetoxymethyl)-3-aminotetrahydro-2H-pyran-2,4,5-triyl triacetate

(+)-D-glucosamine hydrochloride

Downstream raw materials:

Allyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosid