Benzoic acid (R)-2-((3aR,5S,6R,6aR)-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-ethyl ester

Base Information

• Chemical Name: Benzoic acid (R)-2-((3aR,5S,6R,6aR)-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-ethyl ester
• CAS No.: 377079-40-8
• Molecular Formula: C₂₄H₂₈O₇
• Molecular Weight: 428.482
• Mol file: 377079-40-8.mol

Synonyms:

Chemical Property of Benzoic acid (R)-2-((3aR,5S,6R,6aR)-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (R)-2-((3aR,5S,6R,6aR)-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-ethyl ester

There total 6 articles about Benzoic acid (R)-2-((3aR,5S,6R,6aR)-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-ethyl 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: 52.0%

benzoyl chloride (98-88-4) + 3-C-(benzyloxymethyl)-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose (85315-68-0) → Benzoic acid (R)-2-((3aR,5S,6R,6aR)-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-ethyl ester (377079-40-8)

Guidance literature:

DOI:10.1081/NCN-100002354

Reference yield:

O1,O2;O5,O6-diisopropylidene-3-methylene-α-D-ribo-3-deoxy-hexofuranose (21665-16-7) → Benzoic acid (R)-2-((3aR,5S,6R,6aR)-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-ethyl ester (377079-40-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: BH₃

1.2: 77 percent / H₂O₂

2.1: aq. AcOH

With borane; acetic acid;

DOI:10.1081/NCN-100002354

Reference yield:

((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol (69832-48-0) → Benzoic acid (R)-2-((3aR,5S,6R,6aR)-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-ethyl ester (377079-40-8)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. AcOH

With acetic acid;

DOI:10.1081/NCN-100002354

upstream raw materials:

benzoyl chloride

3-C-(benzyloxymethyl)-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose

((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol

O¹,O²;O⁵,O⁶-diisopropylidene-3-methylene-α-D-ribo-3-deoxy-hexofuranose

Downstream raw materials:

C₄₀H₄₂N₂O₁₁S₂

Benzoic acid (R)-2-[(2S,3R,4R,5R)-4-acetoxy-3-benzyloxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-2-benzyloxy-ethyl ester

Benzoic acid (R)-2-benzyloxy-2-((2S,3R,4R)-4,5-diacetoxy-3-benzyloxymethyl-tetrahydro-furan-2-yl)-ethyl ester

1-[(2R,3R,4S,5S)-5-((R)-1-Benzyloxy-2-hydroxy-ethyl)-4-benzyloxymethyl-3-hydroxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione