tert-butyl (3aS,4R,6R,6aR)-tetrahydro-4-[(methoxymethoxy)methyl]-2,2-dimethyl-6-[(trityloxy)methyl]-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate

Base Information

• Chemical Name: tert-butyl (3aS,4R,6R,6aR)-tetrahydro-4-[(methoxymethoxy)methyl]-2,2-dimethyl-6-[(trityloxy)methyl]-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
• CAS No.: 704902-02-3
• Molecular Formula: C₃₅H₄₃NO₇
• Molecular Weight: 589.729
• Mol file: 704902-02-3.mol

Synonyms:tert-butyl (3aS,4R,6R,6aR)-tetrahydro-4-[(methoxymethoxy)methyl]-2,2-dimethyl-6-[(trityloxy)methyl]-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate

Chemical Property of tert-butyl (3aS,4R,6R,6aR)-tetrahydro-4-[(methoxymethoxy)methyl]-2,2-dimethyl-6-[(trityloxy)methyl]-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (3aS,4R,6R,6aR)-tetrahydro-4-[(methoxymethoxy)methyl]-2,2-dimethyl-6-[(trityloxy)methyl]-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate

There total 1 articles about tert-butyl (3aS,4R,6R,6aR)-tetrahydro-4-[(methoxymethoxy)methyl]-2,2-dimethyl-6-[(trityloxy)methyl]-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate 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: 62.0%

chloromethyl methyl ether (107-30-2) + (2R,3R,4S,5R)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-hydroxymethylpyrrolidine (212892-52-9) → tert-butyl (3aS,4R,6R,6aR)-tetrahydro-4-[(methoxymethoxy)methyl]-2,2-dimethyl-6-[(trityloxy)methyl]-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate (704902-02-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1002/hlca.200490078

Reference yield:

tert-butyl (3aS,4R,6R,6aR)-tetrahydro-4-[(methoxymethoxy)methyl]-2,2-dimethyl-6-[(trityloxy)methyl]-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate (704902-02-3) → (2R,3R,4S,5R)-2-[(benzylamino)methyl]-5-(hydroxymethyl)pyrrolidine-3,4-diol

Guidance literature:

Multi-step reaction with 4 steps

1: 76 percent / Na; liq. NH₃ / tetrahydrofuran / -78 °C

2: (COCl)2; Et₃N; DMSO / CH₂Cl₂ / -78 - -30 °C

3: 55 mg / NaBH(OAc)3 / 1,2-dichloro-ethane / 20 °C

4: 100 percent / trifluoroacetic acid / H₂O / 0.5 h / 20 °C

With oxalyl dichloride; ammonia; sodium; sodium tris(acetoxy)borohydride; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; 1: Birch reduction;

DOI:10.1002/hlca.200490078

Reference yield:

tert-butyl (3aS,4R,6R,6aR)-tetrahydro-4-[(methoxymethoxy)methyl]-2,2-dimethyl-6-[(trityloxy)methyl]-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate (704902-02-3) → tert-butyl (3aR,4R,6R,6aS)-4-[(benzylamino)methyl]tetrahydro-6-[(methoxymethoxy)methyl]-2,2-dimethyl-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate (704902-04-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / Na; liq. NH₃ / tetrahydrofuran / -78 °C

2: (COCl)2; Et₃N; DMSO / CH₂Cl₂ / -78 - -30 °C

3: 55 mg / NaBH(OAc)3 / 1,2-dichloro-ethane / 20 °C

With oxalyl dichloride; ammonia; sodium; sodium tris(acetoxy)borohydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; 1: Birch reduction;

DOI:10.1002/hlca.200490078

upstream raw materials:

chloromethyl methyl ether

(2R,3R,4S,5R)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-hydroxymethylpyrrolidine

Downstream raw materials:

tert-butyl (3aR,4R,6R,6aS)-4-[(benzylamino)methyl]tetrahydro-6-[(methoxymethoxy)methyl]-2,2-dimethyl-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate