(3aR,4aS,5R,7aS,7bR)-7-Allyl-5-benzyloxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4',5':4,5]furo[3,2-b]pyrrole

Base Information

• Chemical Name: (3aR,4aS,5R,7aS,7bR)-7-Allyl-5-benzyloxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4',5':4,5]furo[3,2-b]pyrrole
• CAS No.: 876175-58-5
• Molecular Formula: C₁₉H₂₅NO₄
• Molecular Weight: 331.412
• Mol file: 876175-58-5.mol

Synonyms:(3aR,4aS,5R,7aS,7bR)-7-Allyl-5-benzyloxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4',5':4,5]furo[3,2-b]pyrrole

Chemical Property of (3aR,4aS,5R,7aS,7bR)-7-Allyl-5-benzyloxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4',5':4,5]furo[3,2-b]pyrrole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4aS,5R,7aS,7bR)-7-Allyl-5-benzyloxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4',5':4,5]furo[3,2-b]pyrrole

There total 3 articles about (3aR,4aS,5R,7aS,7bR)-7-Allyl-5-benzyloxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4',5':4,5]furo[3,2-b]pyrrole 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: 92.0%

(3aR,4aS,5R,7aS,7bR)-7-Allyl-2,2-dimethyl-hexahydro-[1,3]dioxolo[4',5':4,5]furo[3,2-b]pyrrol-5-ol (876175-57-4) + benzyl bromide (100-39-0) → (3aR,4aS,5R,7aS,7bR)-7-Allyl-5-benzyloxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4',5':4,5]furo[3,2-b]pyrrole (876175-58-5)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 0.1h; Heating;

DOI:10.1021/ol052716a

Reference yield:

(R)-1-((3aR,5S,6S,6aR)-6-Allylamino-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol (252053-07-9) → (3aR,4aS,5R,7aS,7bR)-7-Allyl-5-benzyloxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4',5':4,5]furo[3,2-b]pyrrole (876175-58-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / PPh₃; triethylamine / CCl₄; dimethylformamide / 1 h / 25 °C

2: 92 percent / NaH / tetrahydrofuran / 0.1 h / Heating

With sodium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; tetrachloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol052716a

Reference yield:

3-deoxy-3-allylamino-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (252052-99-6) → (3aR,4aS,5R,7aS,7bR)-7-Allyl-5-benzyloxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4',5':4,5]furo[3,2-b]pyrrole (876175-58-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / PPh₃; triethylamine / CCl₄; dimethylformamide / 1 h / 25 °C

2: 92 percent / NaH / tetrahydrofuran / 0.1 h / Heating

With sodium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; tetrachloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol052716a

upstream raw materials:

(3aR,4aS,5R,7aS,7bR)-7-Allyl-2,2-dimethyl-hexahydro-[1,3]dioxolo[4',5':4,5]furo[3,2-b]pyrrol-5-ol

benzyl bromide

(R)-1-((3aR,5S,6S,6aR)-6-Allylamino-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol

3-deoxy-3-allylamino-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Downstream raw materials:

Acetic acid (2S,3S,4R)-2-((R)-1-acetoxy-2,2-bis-ethylsulfanyl-ethyl)-1-allyl-4-benzyloxy-pyrrolidin-3-yl ester

Acetic acid (1S,5R,6S,7R,8R,9R)-6-acetoxy-5-benzyloxy-10-methyl-11-oxa-3,10-diaza-tricyclo[7.2.1.0^3,7]dodec-8-yl ester

Acetic acid (2R,3S,4R)-2-((R)-1-acetoxy-2-hydroxyimino-ethyl)-1-allyl-4-benzyloxy-pyrrolidin-3-yl ester

acetic acid 7-acetoxy-6-benzyloxy-3a,4,6,7,7a,8-hexahydro-3H,5H-2-oxa-1,4a-diaza-s-indacen-8-yl ester