Acetic acid (3S,4R,5R,6S)-4,5-diacetoxy-2-[hydroxy-(2-hydroxy-phenoxy)-phosphoryloxy]-6-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (3S,4R,5R,6S)-4,5-diacetoxy-2-[hydroxy-(2-hydroxy-phenoxy)-phosphoryloxy]-6-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 53919-70-3
• Molecular Formula: C₁₈H₂₃O₁₂P
• Molecular Weight: 462.347
• Mol file: 53919-70-3.mol

Synonyms:

Chemical Property of Acetic acid (3S,4R,5R,6S)-4,5-diacetoxy-2-[hydroxy-(2-hydroxy-phenoxy)-phosphoryloxy]-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 (3S,4R,5R,6S)-4,5-diacetoxy-2-[hydroxy-(2-hydroxy-phenoxy)-phosphoryloxy]-6-methyl-tetrahydro-pyran-3-yl ester

There total 2 articles about Acetic acid (3S,4R,5R,6S)-4,5-diacetoxy-2-[hydroxy-(2-hydroxy-phenoxy)-phosphoryloxy]-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:

o-phenylene chlorophosphate (1499-17-8) + 2,3,4-tri-O-acetyl-L-fucopyranose (28915-80-2,40591-53-5,40591-54-6,40591-55-7,120449-19-6,120449-20-9,143332-42-7,148081-39-4,151413-57-9,151413-58-0) → Acetic acid (3S,4R,5R,6S)-4,5-diacetoxy-2-[hydroxy-(2-hydroxy-phenoxy)-phosphoryloxy]-6-methyl-tetrahydro-pyran-3-yl ester (53919-70-3)

Guidance literature:

With 2,4,6-trimethyl-pyridine; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1139/v81-304

Reference yield:

→ 2,3,4-Tri-O-acetyl-β-L-rhamnopyranosyl-o-hydroxyphenylphosphat (53919-70-3)

Guidance literature:

Aus Pyranose II, o-Phenylenchlorphosphat, 2,6-Lutidin;

DOI:10.1007/BF00923209

Reference yield:

Acetic acid (3S,4R,5R,6S)-4,5-diacetoxy-2-[hydroxy-(2-hydroxy-phenoxy)-phosphoryloxy]-6-methyl-tetrahydro-pyran-3-yl ester (53919-70-3) → Bis(sodium) guanosine 5'-β-L-fucopyranosyl-diphosphate (138552-48-4,143394-77-8,148296-47-3)

Guidance literature:

Multi-step reaction with 2 steps

1: Pb(OAc)4 / dioxane / 0.5 h / 22 °C

2: 1.) pyridine; 2.) tri-n-butylamine; 3.) silver acetate / 1.) water; 2.) tert-butanol, 35-40 deg C, 3 h; 3.) pyridine

With pyridine; lead(IV) acetate; tributyl-amine; silver(I) acetate; In 1,4-dioxane;

DOI:10.1139/v81-304

upstream raw materials:

o-phenylene chlorophosphate

2,3,4-tri-O-acetyl-L-fucopyranose

Downstream raw materials:

Bis(sodium) guanosine 5'-β-L-fucopyranosyl-diphosphate