[(R)-1-((3aS,5S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-nitro-ethyl]-phosphonic acid dimethyl ester

Base Information

• Chemical Name: [(R)-1-((3aS,5S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-nitro-ethyl]-phosphonic acid dimethyl ester
• CAS No.: 141782-03-8
• Molecular Formula: C₁₈H₂₆NO₉P
• Molecular Weight: 431.38
• Mol file: 141782-03-8.mol

Synonyms:

Chemical Property of [(R)-1-((3aS,5S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-nitro-ethyl]-phosphonic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(R)-1-((3aS,5S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-nitro-ethyl]-phosphonic acid dimethyl ester

There total 4 articles about [(R)-1-((3aS,5S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-nitro-ethyl]-phosphonic acid dimethyl 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:

3-O-benzyl-1,2-O-isopropylidene-β-D-altrofuranose (134275-39-1) → [(R)-1-((3aS,5S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-nitro-ethyl]-phosphonic acid dimethyl ester (141782-03-8)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium periodate / H₂O; methanol / 1 h / Ambient temperature

2: MeONa / methanol / 2 h / 0 °C

3: Ac₂O, AcONa / 10 h / Ambient temperature

4: triethylamine / 3 h / 25 °C

With sodium periodate; sodium methylate; sodium acetate; acetic anhydride; triethylamine; In methanol; water;

DOI:10.1246/bcsj.65.1154

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-β-D-arabino-pentodialdo-1,4-furanose (110316-24-0) → [(R)-1-((3aS,5S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-nitro-ethyl]-phosphonic acid dimethyl ester (141782-03-8)

Guidance literature:

Multi-step reaction with 3 steps

1: MeONa / methanol / 2 h / 0 °C

2: Ac₂O, AcONa / 10 h / Ambient temperature

3: triethylamine / 3 h / 25 °C

With sodium methylate; sodium acetate; acetic anhydride; triethylamine; In methanol;

DOI:10.1246/bcsj.65.1154

Reference yield:

(3aS,5R,6R,6aS)-6-Benzyloxy-2,2-dimethyl-5-((E)-2-nitro-vinyl)-tetrahydro-furo[2,3-d][1,3]dioxole (141782-01-6) + Dimethyl phosphite (868-85-9) → [(R)-1-((3aS,5S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-nitro-ethyl]-phosphonic acid dimethyl ester (141782-03-8) + [(S)-1-((3aS,5S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-nitro-ethyl]-phosphonic acid dimethyl ester (141782-04-9)

Guidance literature:

With triethylamine; at 25 ℃; for 3h; Yield given. Yields of byproduct given;

DOI:10.1246/bcsj.65.1154

upstream raw materials:

(3aS,5R,6R,6aS)-6-Benzyloxy-2,2-dimethyl-5-((E)-2-nitro-vinyl)-tetrahydro-furo[2,3-d][1,3]dioxole

Dimethyl phosphite

3-O-benzyl-1,2-O-isopropylidene-β-D-altrofuranose

1-((3aS,5R,6R,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-nitro-ethanol

Downstream raw materials:

3-O-benzyl-5,6-dideoxy-5-C-(dimethoxyphosphinyl)-1,2-O-isopropylidene-α-D-xylo-hexo-5-enofuranose