D-glycero-L-manno-Heptonic acid, 2,6-anhydro-, 3,4,7-triacetate

Base Information

• Chemical Name: D-glycero-L-manno-Heptonic acid, 2,6-anhydro-, 3,4,7-triacetate
• CAS No.: 228115-82-0
• Molecular Formula: C₁₃H₁₈O₁₀
• Molecular Weight: 334.28
• Mol file: 228115-82-0.mol

Synonyms:D-glycero-L-manno-Heptonic acid, 2,6-anhydro-, 3,4,7-triacetate

Chemical Property of D-glycero-L-manno-Heptonic acid, 2,6-anhydro-, 3,4,7-triacetate

Chemical Property:

• PSA: 145.66000
• LogP: -1.37420

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of D-glycero-L-manno-Heptonic acid, 2,6-anhydro-, 3,4,7-triacetate

There total 1 articles about D-glycero-L-manno-Heptonic acid, 2,6-anhydro-, 3,4,7-triacetate 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:

Acetic acid (1S,4R,6R,7S,8R)-8-acetoxy-6-acetoxymethyl-3-oxo-2,5-dioxa-bicyclo[2.2.2]oct-7-yl ester (228115-81-9) → 3,4,7-tri-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptonic acid (228115-82-0)

Guidance literature:

With water;

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

Reference yield:

3,4,7-tri-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptonic acid (228115-82-0) → Acetic acid (4aS,8aS,9R,9aS,10aR)-2,7-diphenyl-hexahydro-1,3,6,8,10-pentaoxa-anthracen-9-yl ester (71072-13-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: acetic anhydride; sodium acetate / Heating

2.1: lithium aluminum hydride / tetrahydrofuran / 2 h / Heating

2.2: 21.2 g / pyridine

3.1: 85 percent / sodium methoxide; methanol / 20 h

4.1: TsOH

5.1: pyridine

With pyridine; methanol; lithium aluminium tetrahydride; sodium methylate; sodium acetate; acetic anhydride; toluene-4-sulfonic acid; In tetrahydrofuran; 1.1: Cyclization / 2.1: Reduction / 2.2: Acetylation / 3.1: Deacetylation / 4.1: acetalization / 5.1: Acetylation;

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

Reference yield:

3,4,7-tri-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptonic acid (228115-82-0) → 2,6-anhydro-4-azido-1,3:5,7-di-O-benzylidene-4-deoxy-L-glycero-L-gluco-heptitol (228115-96-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: acetic anhydride; sodium acetate / Heating

2.1: lithium aluminum hydride / tetrahydrofuran / 2 h / Heating

2.2: 21.2 g / pyridine

3.1: 85 percent / sodium methoxide; methanol / 20 h

4.1: TsOH

5.1: 73 percent / 4-(dimethylamino)pyridine; pyridine / 3 h / 70 °C

6.1: 10 percent / sodium azide / dimethylsulfoxide / 1 h / 180 °C

With pyridine; methanol; dmap; lithium aluminium tetrahydride; sodium azide; sodium methylate; sodium acetate; acetic anhydride; toluene-4-sulfonic acid; In tetrahydrofuran; dimethyl sulfoxide; 1.1: Cyclization / 2.1: Reduction / 2.2: Acetylation / 3.1: Deacetylation / 4.1: acetalization / 5.1: Tosylation / 6.1: Substitution;

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

upstream raw materials:

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:

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

1,3,4,5,7-penta-O-acetyl-2,6-anhydro-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