Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((2R,3S,4R,5R,6R)-3-acetylamino-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-ylsulfanyl)-6-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((2R,3S,4R,5R,6R)-3-acetylamino-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-ylsulfanyl)-6-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 189683-17-8
• Molecular Formula: C₂₇H₃₇NO₁₂S
• Molecular Weight: 599.656
• Mol file: 189683-17-8.mol

Synonyms:Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((2R,3S,4R,5R,6R)-3-acetylamino-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-ylsulfanyl)-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((2R,3S,4R,5R,6R)-3-acetylamino-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-ylsulfanyl)-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((2R,3S,4R,5R,6R)-3-acetylamino-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-ylsulfanyl)-6-methyl-tetrahydro-pyran-3-yl ester

There total 10 articles about Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((2R,3S,4R,5R,6R)-3-acetylamino-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-ylsulfanyl)-6-methyl-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: 73.0%

Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((4aR,6R,7S,8R,8aR)-7-acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ylsulfanyl)-6-methyl-tetrahydro-pyran-3-yl ester → Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((2R,3S,4R,5R,6R)-3-acetylamino-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-ylsulfanyl)-6-methyl-tetrahydro-pyran-3-yl ester (189683-17-8)

Guidance literature:

With camphor-10-sulfonic acid; In methanol; at 50 ℃; for 1.5h;

DOI:10.1016/S0040-4020(97)00246-9

Reference yield:

benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (10375-65-2,13318-46-2,13343-66-3,19374-72-2,33423-34-6,34029-78-2,41355-94-6,110911-57-4,141019-71-8) → Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((2R,3S,4R,5R,6R)-3-acetylamino-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-ylsulfanyl)-6-methyl-tetrahydro-pyran-3-yl ester (189683-17-8)

Guidance literature:

Multi-step reaction with 7 steps

1: NaOMe / methanol / 1 h / Ambient temperature

2: 33.5 g / p-TsOH*H₂O / acetonitrile / 14 h / Ambient temperature

3: 1) MsCl, 2) NaOAc*3H₂O / 1) CH₂Cl₂, pyridine, room temperature, 28 h, 2) 2-methoxyethanol, H₂O, 130 deg C, 18 h

4: 72 percent / NaH, 1,1'-sulfonyldiimidazole / tetrahydrofuran / 15 h / Ambient temperature

5: 98 percent / pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

6: 61 percent / NaH / dimethylformamide / 0.5 h / 20 °C

7: 73 percent / camphorsulfonic acid / methanol / 1.5 h / 50 °C

With pyridine; camphor-10-sulfonic acid; sodium methylate; sodium acetate; sodium hydride; toluene-4-sulfonic acid; methanesulfonyl chloride; N,N`-sulfuryldiimidazole; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(97)00246-9

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((2R,3S,4R,5R,6R)-3-acetylamino-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-ylsulfanyl)-6-methyl-tetrahydro-pyran-3-yl ester (189683-17-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 61 percent / 4 Angstroem molecular sieves, SnCl₄ / acetonitrile / 14 h / 75 °C

2: NaOMe / methanol / 1 h / Ambient temperature

3: 33.5 g / p-TsOH*H₂O / acetonitrile / 14 h / Ambient temperature

4: 1) MsCl, 2) NaOAc*3H₂O / 1) CH₂Cl₂, pyridine, room temperature, 28 h, 2) 2-methoxyethanol, H₂O, 130 deg C, 18 h

5: 72 percent / NaH, 1,1'-sulfonyldiimidazole / tetrahydrofuran / 15 h / Ambient temperature

6: 98 percent / pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

7: 61 percent / NaH / dimethylformamide / 0.5 h / 20 °C

8: 73 percent / camphorsulfonic acid / methanol / 1.5 h / 50 °C

With pyridine; 4 A molecular sieve; camphor-10-sulfonic acid; sodium methylate; sodium acetate; tin(IV) chloride; sodium hydride; toluene-4-sulfonic acid; methanesulfonyl chloride; N,N`-sulfuryldiimidazole; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(97)00246-9

upstream raw materials:

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

benzyl 2-acetamido-3,6-di-O-benzoyl-β-D-allopyranoside

N-((4aR,6R,7R,8S,8aS)-6-Benzyloxy-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide