p-iodophenyl-2,3,6,-tri-O-acetyl-4-O-(2,3-di-O-acetyl-6-O-benzoyl-4-thio-α-D-glucopyranosyl)-α-D-glucopyranoside

Base Information

• Chemical Name: p-iodophenyl-2,3,6,-tri-O-acetyl-4-O-(2,3-di-O-acetyl-6-O-benzoyl-4-thio-α-D-glucopyranosyl)-α-D-glucopyranoside
• CAS No.: 119803-61-1
• Molecular Formula: C₃₅H₃₉IO₁₆S
• Molecular Weight: 874.656

Synonyms:p-iodophenyl-2,3,6,-tri-O-acetyl-4-O-(2,3-di-O-acetyl-6-O-benzoyl-4-thio-α-D-glucopyranosyl)-α-D-glucopyranoside

Chemical Property of p-iodophenyl-2,3,6,-tri-O-acetyl-4-O-(2,3-di-O-acetyl-6-O-benzoyl-4-thio-α-D-glucopyranosyl)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-iodophenyl-2,3,6,-tri-O-acetyl-4-O-(2,3-di-O-acetyl-6-O-benzoyl-4-thio-α-D-glucopyranosyl)-α-D-glucopyranoside

There total 9 articles about p-iodophenyl-2,3,6,-tri-O-acetyl-4-O-(2,3-di-O-acetyl-6-O-benzoyl-4-thio-α-D-glucopyranosyl)-α-D-glucopyranoside 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%

p-iodophenyl-2,3,6-tri-O-acetyl-4-O-(2,3-di-O-acetyl-4-S-acetyl-6-O-benzoyl-4-thio-α-D-glucopyranosyl)-α-D-glucopyranosyde (119803-59-7) → p-iodophenyl-2,3,6,-tri-O-acetyl-4-O-(2,3-di-O-acetyl-6-O-benzoyl-4-thio-α-D-glucopyranosyl)-α-D-glucopyranoside (119803-61-1)

Guidance literature:

With 1,4-dithio-erythritol; Cysteamine; In N,N,N,N,N,N-hexamethylphosphoric triamide; for 0.666667h; Ambient temperature;

Reference yield:

1,2,3,6-tetra-O-acetyl-4-O-(2',3'-di-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside (72718-62-8,81661-67-8,102281-77-6,120852-02-0,93417-43-7) → p-iodophenyl-2,3,6,-tri-O-acetyl-4-O-(2,3-di-O-acetyl-6-O-benzoyl-4-thio-α-D-glucopyranosyl)-α-D-glucopyranoside (119803-61-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 73 percent / triethylamine / CH₂Cl₂ / 24 h / Ambient temperature

2: pyridine / CH₂Cl₂ / 0.5 h / 0 °C

3: 51 percent / sodium nitrite / dimethylformamide / 3 h / Ambient temperature

4: 97 percent / pyridine / CH₂Cl₂ / 0 deg C, , 30 min, RT, 3 h

5: tin tetrachloride / CHCl₃; nitromethane / 1.5 h / Ambient temperature

6: pyridine / methanol; CH₂Cl₂ / 24 h / Ambient temperature

7: pyridine / CH₂Cl₂

8: 44 percent / tetrahydrofuran / 24 h / Ambient temperature

9: 75 percent / 1,4-dithioerythritol, cysteamine / hexamethylphosphoric acid triamide / 0.67 h / Ambient temperature

With pyridine; 1,4-dithio-erythritol; tin(IV) chloride; triethylamine; Cysteamine; sodium nitrite; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; nitromethane; dichloromethane; chloroform; N,N-dimethyl-formamide;

Reference yield:

1,2,3,6-tetra-O-acetyl-4-O-(2,3-di-O-acetyl-6-O-benzoyl-α-D-glucopyranosyl)-β-D-glucopyranose (119803-50-8) → p-iodophenyl-2,3,6,-tri-O-acetyl-4-O-(2,3-di-O-acetyl-6-O-benzoyl-4-thio-α-D-glucopyranosyl)-α-D-glucopyranoside (119803-61-1)

Guidance literature:

Multi-step reaction with 8 steps

1: pyridine / CH₂Cl₂ / 0.5 h / 0 °C

2: 51 percent / sodium nitrite / dimethylformamide / 3 h / Ambient temperature

3: 97 percent / pyridine / CH₂Cl₂ / 0 deg C, , 30 min, RT, 3 h

4: tin tetrachloride / CHCl₃; nitromethane / 1.5 h / Ambient temperature

5: pyridine / methanol; CH₂Cl₂ / 24 h / Ambient temperature

6: pyridine / CH₂Cl₂

7: 44 percent / tetrahydrofuran / 24 h / Ambient temperature

8: 75 percent / 1,4-dithioerythritol, cysteamine / hexamethylphosphoric acid triamide / 0.67 h / Ambient temperature

With pyridine; 1,4-dithio-erythritol; tin(IV) chloride; Cysteamine; sodium nitrite; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; nitromethane; dichloromethane; chloroform; N,N-dimethyl-formamide;

upstream raw materials:

p-iodophenyl-2,3,6-tri-O-acetyl-4-O-(2,3-di-O-acetyl-4-S-acetyl-6-O-benzoyl-4-thio-α-D-glucopyranosyl)-α-D-glucopyranosyde

1,2,3,6-tetra-O-acetyl-4-O-(2',3'-di-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside

1,2,3,6-tetra-O-acetyl-4-O-(2,3-di-O-acetyl-6-O-benzoyl-α-D-glucopyranosyl)-β-D-glucopyranose

Benzoic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-[(2R,3R,4S,5R)-4,5-diacetoxy-2-acetoxymethyl-6-(4-iodo-phenoxy)-tetrahydro-pyran-3-yloxy]-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester

Downstream raw materials:

Benzoic acid (2R,3R,4R,5R,6S)-4,5-diacetoxy-3-((5S,6R)-5-acetoxy-6-acetoxymethyl-5,6-dihydro-2H-pyran-2-ylsulfanyl)-6-[(2R,3R,4S,5R)-4,5-diacetoxy-2-acetoxymethyl-6-(4-iodo-phenoxy)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-2-ylmethyl ester

C₂₄H₃₃IO₁₃S

p-iodophenyl 4-O-<4-S-(2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-4-thio-α-D-glucopyranosyl>-α-D-glucopyranoside

C₂₄H₃₃IO₁₃S

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