(2R,3S,4S,5R,6R)-6-((2R,3R,4R,5R,6S)-3-Acetoxy-5-acetylamino-6-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzoyloxy-4-benzyloxy-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2R,3S,4S,5R,6R)-6-((2R,3R,4R,5R,6S)-3-Acetoxy-5-acetylamino-6-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzoyloxy-4-benzyloxy-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 206752-01-4
• Molecular Formula: C₄₅H₄₉NO₁₄
• Molecular Weight: 827.882
• Mol file: 206752-01-4.mol

Synonyms:(2R,3S,4S,5R,6R)-6-((2R,3R,4R,5R,6S)-3-Acetoxy-5-acetylamino-6-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzoyloxy-4-benzyloxy-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property of (2R,3S,4S,5R,6R)-6-((2R,3R,4R,5R,6S)-3-Acetoxy-5-acetylamino-6-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzoyloxy-4-benzyloxy-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S,5R,6R)-6-((2R,3R,4R,5R,6S)-3-Acetoxy-5-acetylamino-6-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzoyloxy-4-benzyloxy-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 5 articles about (2R,3S,4S,5R,6R)-6-((2R,3R,4R,5R,6S)-3-Acetoxy-5-acetylamino-6-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzoyloxy-4-benzyloxy-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl 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: 75.0%

(2R,3S,4S,5R,6R)-6-((2R,3R,4R,5R,6S)-3-Acetoxy-5-acetylamino-6-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzoyloxy-4-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (206751-97-5) → (2R,3S,4S,5R,6R)-6-((2R,3R,4R,5R,6S)-3-Acetoxy-5-acetylamino-6-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzoyloxy-4-benzyloxy-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester (206752-01-4)

Guidance literature:

With pyridine; thiourea; In ethanol; at 80 ℃; for 24h;

DOI:10.1016/S0008-6215(97)10017-9

Reference yield:

benzyl bromide (100-39-0) → (2R,3S,4S,5R,6R)-6-((2R,3R,4R,5R,6S)-3-Acetoxy-5-acetylamino-6-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzoyloxy-4-benzyloxy-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester (206752-01-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / BaO, Ba(OH)2*8H₂O / dimethylformamide / 20 h / Ambient temperature

2: 89 percent / acetic acid / H₂O / 0.5 h / 100 °C

3: 1.) (+/-)-camphor-10-sulfonic acid, 2.) acetic acid / 1.) toluene, room temperature, 1 h, 2.) water, room temperature, 10 min

4: 1.) molecular sieves 4A, 2.) trimethylsilyl triflate / 1.) CH₂Cl₂, room temperature, 40 min, 2.) CH₂Cl₂, toluene, 0 deg C

5: 75 percent / thiourea, pyridine / ethanol / 24 h / 80 °C

With pyridine; barium dihydroxide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; acetic acid; thiourea; barium(II) oxide; In ethanol; water; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(97)10017-9

Reference yield:

benzyl 2-acetamido-2-deoxy-3,4-O-isopropylidene-α-D-galactopyranoside (112289-51-7) → (2R,3S,4S,5R,6R)-6-((2R,3R,4R,5R,6S)-3-Acetoxy-5-acetylamino-6-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzoyloxy-4-benzyloxy-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester (206752-01-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / BaO, Ba(OH)2*8H₂O / dimethylformamide / 20 h / Ambient temperature

2: 89 percent / acetic acid / H₂O / 0.5 h / 100 °C

3: 1.) (+/-)-camphor-10-sulfonic acid, 2.) acetic acid / 1.) toluene, room temperature, 1 h, 2.) water, room temperature, 10 min

4: 1.) molecular sieves 4A, 2.) trimethylsilyl triflate / 1.) CH₂Cl₂, room temperature, 40 min, 2.) CH₂Cl₂, toluene, 0 deg C

5: 75 percent / thiourea, pyridine / ethanol / 24 h / 80 °C

With pyridine; barium dihydroxide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; acetic acid; thiourea; barium(II) oxide; In ethanol; water; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(97)10017-9

upstream raw materials:

(2R,3S,4S,5R,6R)-6-((2R,3R,4R,5R,6S)-3-Acetoxy-5-acetylamino-6-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzoyloxy-4-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

benzyl bromide

benzyl 2-acetamido-2-deoxy-3,4-O-isopropylidene-α-D-galactopyranoside

benzyl 2-acetamido-6-O-benzyl-2-deoxy-α-D-galactopyranoside

Downstream raw materials:

(2R,3S,4R,5R,6R)-6-((2S,3R,4R,5R,6R)-3-Acetylamino-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yloxy)-4-benzyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid

(2R,3S,4S,5R,6R)-6-((2R,3R,4R,5R,6S)-3-Acetoxy-5-acetylamino-6-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzoyloxy-4-benzyloxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester