L-glycero-L-galacto-Heptitol, 2,6-anhydro-, pentaacetate

Base Information

• Chemical Name: L-glycero-L-galacto-Heptitol, 2,6-anhydro-, pentaacetate
• CAS No.: 115224-88-9
• Molecular Formula: C₁₇H₂₄O₁₁
• Molecular Weight: 404.371
• Mol file: 115224-88-9.mol

Synonyms:L-glycero-L-galacto-Heptitol, 2,6-anhydro-, pentaacetate

Chemical Property of L-glycero-L-galacto-Heptitol, 2,6-anhydro-, pentaacetate

Chemical Property:

• PSA: 140.73000
• LogP: -0.32490

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-glycero-L-galacto-Heptitol, 2,6-anhydro-, pentaacetate

There total 10 articles about L-glycero-L-galacto-Heptitol, 2,6-anhydro-, pentaacetate 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: 51.0%

C22H27NO11S + acetic acid (64-19-7,77671-22-8) → 1,3,4,5,7-penta-O-acetyl-2,6-anhydro-L-glycero-L-galacto-heptitol (115224-88-9)

Guidance literature:

With potassium phosphate; In 1,4-dioxane; Reflux;

DOI:10.1039/c6ra27282g

Reference yield:

3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptonitrile (52443-07-9) → 1,3,4,5,7-penta-O-acetyl-2,6-anhydro-L-glycero-L-galacto-heptitol (115224-88-9)

Guidance literature:

Multi-step reaction with 4 steps

1: NaH₂PO₂ / Raney nickel

2: p-toluenesulfonic acid monohydrate / CH₂Cl₂; acetone / 0.33 h

3: sodium borohydride / methanol / 0.33 h

4: 287 mg / pyridine

With pyridine; sodium tetrahydroborate; sodium hypophosphite; toluene-4-sulfonic acid; nickel; In methanol; dichloromethane; acetone; 1: Reduction / 2: Hydrolysis / 3: Reduction / 4: Acetylation;

DOI:10.1016/S0040-4020(99)00327-0

Reference yield:

β-D-galactose peracetate (4163-60-4) → 1,3,4,5,7-penta-O-acetyl-2,6-anhydro-L-glycero-L-galacto-heptitol (115224-88-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent Chromat_. / Co₂(CO)8 / CH₂Cl₂ / 144 h / 10 °C / 760 Torr

2: CDCl₃ / 40 h / 50 °C / Irradiation

With dicobalt octacarbonyl; In chloroform-d1; dichloromethane;

DOI:10.1021/jo00249a059

upstream raw materials:

Acetic acid (2R,3S,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-trimethylsilanyloxymethyl-tetrahydro-pyran-4-yl ester

acetyl chloride

acetic anhydride

Acetic acid (1S,4R,6R,7S,8R)-8-acetoxy-6-acetoxymethyl-3-oxo-2,5-dioxa-bicyclo[2.2.2]oct-7-yl ester

Downstream raw materials:

2,6-anhydro-1,7-di-O-(p-toluenesulfonyl)-L-glycero-L-galacto-heptitol

2,6-anhydro-1,4,7-tri-O-(p-toluenesulfonyl)-L-glycero-L-galacto-heptitol

(4aS,8aR,9R,9aR,10aR)-2,7-Diphenyl-hexahydro-1,3,6,8,10-pentaoxa-anthracen-9-ol

Acetic acid (4aS,8aS,9R,9aS,10aR)-2,7-diphenyl-hexahydro-1,3,6,8,10-pentaoxa-anthracen-9-yl ester

Refernces

• 1、 Dent, Barry R.,Furneaux, Richard H.,Gainsford, Graeme J.,Lynch, Gregory P.. "Synthesis studies of structural analogues of tagetitoxin: 4-O-acetyl-3- amino-1,6-anhydro-3-deoxy-D-gulose 2-phosphate". . p. 6977 - 6996. Retrieved 2007/10/03.