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

Base Information

• Chemical Name: Chloro-methanesulfonic acid (S)-1-[(2S,3R,4S,5S)-3,4-bis-benzyloxy-5-(2-hydroxy-ethyl)-tetrahydro-furan-2-yl]-propyl ester
• CAS No.: 273723-55-0
• Molecular Formula: C₂₄H₃₁ClO₇S
• Molecular Weight: 499.025
• Mol file: 273723-55-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about Chloro-methanesulfonic acid (S)-1-[(2S,3R,4S,5S)-3,4-bis-benzyloxy-5-(2-hydroxy-ethyl)-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:

Chloro-methanesulfonic acid (S)-1-[(2S,3R,4S,5S)-3,4-bis-benzyloxy-5-(2-trityloxy-ethyl)-tetrahydro-furan-2-yl]-propyl ester → Chloro-methanesulfonic acid (S)-1-[(2S,3R,4S,5S)-3,4-bis-benzyloxy-5-(2-hydroxy-ethyl)-tetrahydro-furan-2-yl]-propyl ester (273723-55-0)

Guidance literature:

With hydrogenchloride; In methanol; dichloromethane; at 20 ℃;

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) → Chloro-methanesulfonic acid (S)-1-[(2S,3R,4S,5S)-3,4-bis-benzyloxy-5-(2-hydroxy-ethyl)-tetrahydro-furan-2-yl]-propyl ester (273723-55-0)

Guidance literature:

Multi-step reaction with 10 steps

1: DMAP / pyridine; CH₂Cl₂ / 20 °C

2: H₂SO₄ / acetic acid / 0 °C

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

4: K₂CO₃ / methanol / 96 h / 20 °C

5: NaH; Bu₄NI / dimethylformamide / 0 °C

6: O₃ / methanol; CH₂Cl₂

7: 2,6-lutidine / CH₂Cl₂ / 20 °C

8: LiAlH₄ / diethyl ether / 0 °C

9: 2,6-lutidine / CH₂Cl₂ / 20 °C

10: HCl / methanol; CH₂Cl₂ / 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; dmap; lithium aluminium tetrahydride; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; ozone; In pyridine; methanol; diethyl ether; dichloromethane; acetic acid; N,N-dimethyl-formamide; 1: Acylation / 2: Acetylation / 3: Alkylation / 4: Hydrolysis / 5: Alkylation / 6: Oxidation / 7: Etherification / 8: Reduction / 9: Alkylation / 10: Hydrolysis;

DOI:10.3987/com-99-s148

Reference yield:

2,2-Dimethyl-propionic acid (S)-1-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-propyl ester → Chloro-methanesulfonic acid (S)-1-[(2S,3R,4S,5S)-3,4-bis-benzyloxy-5-(2-hydroxy-ethyl)-tetrahydro-furan-2-yl]-propyl ester (273723-55-0)

Guidance literature:

Multi-step reaction with 9 steps

1: H₂SO₄ / acetic acid / 0 °C

2: 93 percent / TMSOTf / CH₂Cl₂ / 48 h / -15 - 0 °C

3: K₂CO₃ / methanol / 96 h / 20 °C

4: NaH; Bu₄NI / dimethylformamide / 0 °C

5: O₃ / methanol; CH₂Cl₂

6: 2,6-lutidine / CH₂Cl₂ / 20 °C

7: LiAlH₄ / diethyl ether / 0 °C

8: 2,6-lutidine / CH₂Cl₂ / 20 °C

9: HCl / methanol; CH₂Cl₂ / 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; lithium aluminium tetrahydride; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; ozone; In methanol; diethyl ether; dichloromethane; acetic acid; N,N-dimethyl-formamide; 1: Acetylation / 2: Alkylation / 3: Hydrolysis / 4: Alkylation / 5: Oxidation / 6: Etherification / 7: Reduction / 8: Alkylation / 9: Hydrolysis;

DOI:10.3987/com-99-s148

upstream raw materials:

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

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

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

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