ethyl [methyl (2-O-acetyl-3,4-di-O-methyl-β-D-glucopyranosyl)uronate]-(1->3)-3-C-methyl-2,4-di-O-methyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside

Base Information

• Chemical Name: ethyl [methyl (2-O-acetyl-3,4-di-O-methyl-β-D-glucopyranosyl)uronate]-(1->3)-3-C-methyl-2,4-di-O-methyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside
• CAS No.: 904326-31-4
• Molecular Formula: C₄₂H₆₀O₁₅S
• Molecular Weight: 836.995
• Mol file: 904326-31-4.mol

Synonyms:ethyl [methyl (2-O-acetyl-3,4-di-O-methyl-β-D-glucopyranosyl)uronate]-(1->3)-3-C-methyl-2,4-di-O-methyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside

Chemical Property of ethyl [methyl (2-O-acetyl-3,4-di-O-methyl-β-D-glucopyranosyl)uronate]-(1->3)-3-C-methyl-2,4-di-O-methyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl [methyl (2-O-acetyl-3,4-di-O-methyl-β-D-glucopyranosyl)uronate]-(1->3)-3-C-methyl-2,4-di-O-methyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside

There total 11 articles about ethyl [methyl (2-O-acetyl-3,4-di-O-methyl-β-D-glucopyranosyl)uronate]-(1->3)-3-C-methyl-2,4-di-O-methyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside 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: 35.0%

(2S,3S,4S,5R,6S)-5-Acetoxy-6-[(2S,3S,4R,5R)-3,5-dimethoxy-2,4-dimethyl-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yloxy]-3,4-dimethoxy-tetrahydro-pyran-2-carboxylic acid methyl ester (904326-17-6) + ethyl 2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside (156626-44-7) → ethyl [methyl (2-O-acetyl-3,4-di-O-methyl-β-D-glucopyranosyl)uronate]-(1->3)-3-C-methyl-2,4-di-O-methyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside (904326-31-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -50 ℃; for 0.5h;

DOI:10.1016/j.carres.2006.04.038

Reference yield:

2,6-di-O-acetyl-3,4-di-O-methyl-D-glucopyranose → ethyl [methyl (2-O-acetyl-3,4-di-O-methyl-β-D-glucopyranosyl)uronate]-(1->3)-3-C-methyl-2,4-di-O-methyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside (904326-31-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 61 percent / K₂CO₃ / CH₂Cl₂ / 24 h / 20 °C

2: 42 percent / TMSOTf / CH₂Cl₂ / 0.5 h / -50 °C

3: 86 percent / NaOCH₃ / methanol / 8 h / 20 °C

4: H₂SO₄; CrO₃ / acetone / 1 h / 20 °C

5: 46 mg / CH₂Cl₂; diethyl ether

6: 67 percent / TFA / acetic acid / 24 h / 65 °C

7: 82 percent / hydrazine acetate / dimethylformamide / 24 h / 20 °C

8: 63 percent / K₂CO₃ / CH₂Cl₂ / 24 h / 20 °C

9: 35 percent / TMSOTf / CH₂Cl₂ / 0.5 h / -50 °C

With chromium(VI) oxide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; sodium methylate; hydrazinium monoacetate; potassium carbonate; trifluoroacetic acid; In methanol; diethyl ether; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetone; 4: Jones oxidation;

DOI:10.1016/j.carres.2006.04.038

Reference yield:

1,2,6-tri-O-acetyl-3,4-di-O-methyl-D-glucopyranose → ethyl [methyl (2-O-acetyl-3,4-di-O-methyl-β-D-glucopyranosyl)uronate]-(1->3)-3-C-methyl-2,4-di-O-methyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside (904326-31-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 92 percent / hydrazine acetate / dimethylformamide / 4 h / 20 °C

2: 61 percent / K₂CO₃ / CH₂Cl₂ / 24 h / 20 °C

3: 42 percent / TMSOTf / CH₂Cl₂ / 0.5 h / -50 °C

4: 86 percent / NaOCH₃ / methanol / 8 h / 20 °C

5: H₂SO₄; CrO₃ / acetone / 1 h / 20 °C

6: 46 mg / CH₂Cl₂; diethyl ether

7: 67 percent / TFA / acetic acid / 24 h / 65 °C

8: 82 percent / hydrazine acetate / dimethylformamide / 24 h / 20 °C

9: 63 percent / K₂CO₃ / CH₂Cl₂ / 24 h / 20 °C

10: 35 percent / TMSOTf / CH₂Cl₂ / 0.5 h / -50 °C

With chromium(VI) oxide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; sodium methylate; hydrazinium monoacetate; potassium carbonate; trifluoroacetic acid; In methanol; diethyl ether; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetone; 5: Jones oxidation;

DOI:10.1016/j.carres.2006.04.038

upstream raw materials:

(2S,3S,4S,5R,6S)-5-Acetoxy-6-[(2S,3S,4R,5R)-3,5-dimethoxy-2,4-dimethyl-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yloxy]-3,4-dimethoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

ethyl 2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside

2,6-di-O-acetyl-3,4-di-O-methyl-β-D-glucopyranosyl trichloroacetimidate

methyl [methyl (2-O-acetyl-3,4-di-O-methyl-β-D-glucopyranosyl)uronate]-(1->3)-3-C-methyl-2,4-di-O-methyl-α-L-rhamnopyranoside