2,2-Dimethyl-propionic acid (2R,3R,4S,4aR,7R,8S,9aR)-3,4,8-tris-benzyloxy-2-benzyloxymethyl-5-oxo-3,4,4a,5,8,9a-hexahydro-2H,7H-1,6,9-trioxa-10-thia-anthracen-7-ylmethyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2R,3R,4S,4aR,7R,8S,9aR)-3,4,8-tris-benzyloxy-2-benzyloxymethyl-5-oxo-3,4,4a,5,8,9a-hexahydro-2H,7H-1,6,9-trioxa-10-thia-anthracen-7-ylmethyl ester
• CAS No.: 260963-55-1
• Molecular Formula: C₄₅H₄₈O₁₀S
• Molecular Weight: 780.936
• Mol file: 260963-55-1.mol

Synonyms:2,2-Dimethyl-propionic acid (2R,3R,4S,4aR,7R,8S,9aR)-3,4,8-tris-benzyloxy-2-benzyloxymethyl-5-oxo-3,4,4a,5,8,9a-hexahydro-2H,7H-1,6,9-trioxa-10-thia-anthracen-7-ylmethyl ester

Chemical Property of 2,2-Dimethyl-propionic acid (2R,3R,4S,4aR,7R,8S,9aR)-3,4,8-tris-benzyloxy-2-benzyloxymethyl-5-oxo-3,4,4a,5,8,9a-hexahydro-2H,7H-1,6,9-trioxa-10-thia-anthracen-7-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (2R,3R,4S,4aR,7R,8S,9aR)-3,4,8-tris-benzyloxy-2-benzyloxymethyl-5-oxo-3,4,4a,5,8,9a-hexahydro-2H,7H-1,6,9-trioxa-10-thia-anthracen-7-ylmethyl ester

There total 10 articles about 2,2-Dimethyl-propionic acid (2R,3R,4S,4aR,7R,8S,9aR)-3,4,8-tris-benzyloxy-2-benzyloxymethyl-5-oxo-3,4,4a,5,8,9a-hexahydro-2H,7H-1,6,9-trioxa-10-thia-anthracen-7-ylmethyl 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: 76.0%

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) + 4-O-benzyl-2-deoxy-1,3-dioxo-6-O-pivaloyl-D-galactopyranose (260963-66-4) → 2,2-Dimethyl-propionic acid (2R,3R,4S,4aR,7R,8S,9aR)-3,4,8-tris-benzyloxy-2-benzyloxymethyl-5-oxo-3,4,4a,5,8,9a-hexahydro-2H,7H-1,6,9-trioxa-10-thia-anthracen-7-ylmethyl ester (260963-55-1)

Guidance literature:

With pyridine; phthalimidesulfenyl chloride; In chloroform; at 20 ℃; for 5h;

DOI:10.1021/jo034556r

Reference yield:

pivaloyl chloride (3282-30-2) → 2,2-Dimethyl-propionic acid (2R,3R,4S,4aR,7R,8S,9aR)-3,4,8-tris-benzyloxy-2-benzyloxymethyl-5-oxo-3,4,4a,5,8,9a-hexahydro-2H,7H-1,6,9-trioxa-10-thia-anthracen-7-ylmethyl ester (260963-55-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 70 percent / pyridine / CH₂Cl₂ / 20 h / 20 °C

2: 72 percent / Bu₄NHSO₄ / acetonitrile; H₂O / 15 h / 65 °C

3: 97 percent / Ag₂CO₃/Celite(R) / benzene / 2.5 h / Heating

4: 87 percent / trifluoroacetic anhydride; DMSO; Et₃N / CH₂Cl₂ / -60 - 20 °C

5: 76 percent / pyridine; phthalimidosulfenyl chloride / CHCl₃ / 5 h / 20 °C

With pyridine; phthalimidesulfenyl chloride; Celite; tetra(n-butyl)ammonium hydrogensulfate; dimethyl sulfoxide; triethylamine; silver carbonate; trifluoroacetic anhydride; In dichloromethane; chloroform; water; acetonitrile; benzene; 5: Diels-Alder reaction;

DOI:10.1021/jo034556r

Reference yield:

benzyl bromide (100-39-0) → 2,2-Dimethyl-propionic acid (2R,3R,4S,4aR,7R,8S,9aR)-3,4,8-tris-benzyloxy-2-benzyloxymethyl-5-oxo-3,4,4a,5,8,9a-hexahydro-2H,7H-1,6,9-trioxa-10-thia-anthracen-7-ylmethyl ester (260963-55-1)

Guidance literature:

Multi-step reaction with 7 steps

1: NaH / dimethylformamide / 3.5 h / 0 - 20 °C

2: 884 mg / TBAF / dimethylformamide / 0 - 20 °C

3: 70 percent / pyridine / CH₂Cl₂ / 20 h / 20 °C

4: 72 percent / Bu₄NHSO₄ / acetonitrile; H₂O / 15 h / 65 °C

5: 97 percent / Ag₂CO₃/Celite(R) / benzene / 2.5 h / Heating

6: 87 percent / trifluoroacetic anhydride; DMSO; Et₃N / CH₂Cl₂ / -60 - 20 °C

7: 76 percent / pyridine; phthalimidosulfenyl chloride / CHCl₃ / 5 h / 20 °C

With pyridine; phthalimidesulfenyl chloride; Celite; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; dimethyl sulfoxide; triethylamine; silver carbonate; trifluoroacetic anhydride; In dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile; benzene; 7: Diels-Alder reaction;

DOI:10.1021/jo034556r

upstream raw materials:

3,4,6-tri-O-benzyl-D-glucal

4-O-benzyl-2-deoxy-1,3-dioxo-6-O-pivaloyl-D-galactopyranose

pivaloyl chloride

benzyl bromide