2,2-Dimethyl-propionic acid (S)-1-((2R,3S,4S,5S)-4-acetoxy-5-allyl-3-benzyloxy-tetrahydro-furan-2-yl)-propyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (S)-1-((2R,3S,4S,5S)-4-acetoxy-5-allyl-3-benzyloxy-tetrahydro-furan-2-yl)-propyl ester
• CAS No.: 273723-50-5
• Molecular Formula: C₂₄H₃₄O₆
• Molecular Weight: 418.53
• Mol file: 273723-50-5.mol

Synonyms:2,2-Dimethyl-propionic acid (S)-1-((2R,3S,4S,5S)-4-acetoxy-5-allyl-3-benzyloxy-tetrahydro-furan-2-yl)-propyl ester

Chemical Property of 2,2-Dimethyl-propionic acid (S)-1-((2R,3S,4S,5S)-4-acetoxy-5-allyl-3-benzyloxy-tetrahydro-furan-2-yl)-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (S)-1-((2R,3S,4S,5S)-4-acetoxy-5-allyl-3-benzyloxy-tetrahydro-furan-2-yl)-propyl ester

There total 5 articles about 2,2-Dimethyl-propionic acid (S)-1-((2R,3S,4S,5S)-4-acetoxy-5-allyl-3-benzyloxy-tetrahydro-furan-2-yl)-propyl 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: 93.0%

2,2-Dimethyl-propionic acid (S)-1-((2R,3S,4R)-4,5-diacetoxy-3-benzyloxy-tetrahydro-furan-2-yl)-propyl ester (273723-48-1) + allyl-trimethyl-silane (762-72-1) → 2,2-Dimethyl-propionic acid (S)-1-((2R,3S,4S,5S)-4-acetoxy-5-allyl-3-benzyloxy-tetrahydro-furan-2-yl)-propyl ester (273723-50-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -15 - 0 ℃; for 48h;

DOI:10.3987/com-99-s148

Reference yield:

(S)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-propan-1-ol (51306-24-2) → 2,2-Dimethyl-propionic acid (S)-1-((2R,3S,4S,5S)-4-acetoxy-5-allyl-3-benzyloxy-tetrahydro-furan-2-yl)-propyl ester (273723-50-5)

Guidance literature:

Multi-step reaction with 3 steps

1: DMAP / pyridine; CH₂Cl₂ / 20 °C

2: H₂SO₄ / acetic acid / 0 °C

3: 93 percent / TMSOTf / CH₂Cl₂ / 48 h / -15 - 0 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; In pyridine; dichloromethane; acetic acid; 1: Acylation / 2: Acetylation / 3: Alkylation;

DOI:10.3987/com-99-s148

Reference yield:

pivaloyl chloride (3282-30-2) → 2,2-Dimethyl-propionic acid (S)-1-((2R,3S,4S,5S)-4-acetoxy-5-allyl-3-benzyloxy-tetrahydro-furan-2-yl)-propyl ester (273723-50-5)

Guidance literature:

Multi-step reaction with 3 steps

1: DMAP / pyridine; CH₂Cl₂ / 20 °C

2: H₂SO₄ / acetic acid / 0 °C

3: 93 percent / TMSOTf / CH₂Cl₂ / 48 h / -15 - 0 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; In pyridine; dichloromethane; acetic acid; 1: Acylation / 2: Acetylation / 3: Alkylation;

DOI:10.3987/com-99-s148

upstream raw materials:

2,2-Dimethyl-propionic acid (S)-1-((2R,3S,4R)-4,5-diacetoxy-3-benzyloxy-tetrahydro-furan-2-yl)-propyl ester

allyl-trimethyl-silane

(S)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-propan-1-ol

pivaloyl chloride

Downstream raw materials:

(S)-1-[(2R,3R,4S,5S)-3,4-Bis-benzyloxy-5-(2-trityloxy-ethyl)-tetrahydro-furan-2-yl]-propan-1-ol

Chloro-methanesulfonic acid (S)-1-[(2S,3R,4S,5S)-3,4-bis-benzyloxy-5-(2-hydroxy-ethyl)-tetrahydro-furan-2-yl]-propyl ester

2,2-Dimethyl-propionic acid (S)-1-[(2R,3R,4S,5S)-3,4-bis-benzyloxy-5-(2-hydroxy-ethyl)-tetrahydro-furan-2-yl]-propyl ester

2,2-Dimethyl-propionic acid (S)-1-((2R,3R,4S,5S)-5-allyl-3-benzyloxy-4-hydroxy-tetrahydro-furan-2-yl)-propyl ester