Acetic acid (2S,3S,3aR,5S,6R,7R,7aR)-3,5,6-triacetoxy-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-7-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3S,3aR,5S,6R,7R,7aR)-3,5,6-triacetoxy-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-7-yl ester
• CAS No.: 131121-24-9
• Molecular Formula: C₂₅H₃₀O₁₂
• Molecular Weight: 522.506

Synonyms:Acetic acid (2S,3S,3aR,5S,6R,7R,7aR)-3,5,6-triacetoxy-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-7-yl ester

Chemical Property of Acetic acid (2S,3S,3aR,5S,6R,7R,7aR)-3,5,6-triacetoxy-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-7-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3S,3aR,5S,6R,7R,7aR)-3,5,6-triacetoxy-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-7-yl ester

There total 9 articles about Acetic acid (2S,3S,3aR,5S,6R,7R,7aR)-3,5,6-triacetoxy-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-7-yl 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:

(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde (33985-40-9) → Acetic acid (2S,3S,3aR,5S,6R,7R,7aR)-3,5,6-triacetoxy-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-7-yl ester (131121-24-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 85 percent

2: 65 percent / NMO / OsO₄, dihydroquinidine p-chlorobenzoate

3: 1) SOCl₂, Et₃N 2) RuCl₃, NaIO₄ / 1) CH₂Cl₂ 2) MeCN, CCl₄, H₂O

4: 2) aq.H₂SO₄ / 1) benzene 2) THF

5: Ba(OMe)2 / methanol

6: PPTS / acetone

7: DIBAH / CH₂Cl₂ / -78 °C

8: 82 percent

9: 1) Dowex 50W 2) pyridine, DMAP / 1) H₂O

With pyridine; dmap; ruthenium trichloride; sodium periodate; thionyl chloride; N-methyl-2-indolinone; Dowex 50W; sulfuric acid; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; barium methoxide; triethylamine; osmium(VIII) oxide; dihydroquinidine 4-chlorobenzoate; In methanol; dichloromethane; acetone;

DOI:10.1016/S0040-4039(00)97476-8

Reference yield:

(E)-ethyl 3-((3aR,4R,6R,6aR)-tetrahydro-4-methoxy-2,2-dimethylfuro[3,4-d][1,3]dioxol-6-yl)acrylate (131121-18-1) → Acetic acid (2S,3S,3aR,5S,6R,7R,7aR)-3,5,6-triacetoxy-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-7-yl ester (131121-24-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 65 percent / NMO / OsO₄, dihydroquinidine p-chlorobenzoate

2: 1) SOCl₂, Et₃N 2) RuCl₃, NaIO₄ / 1) CH₂Cl₂ 2) MeCN, CCl₄, H₂O

3: 2) aq.H₂SO₄ / 1) benzene 2) THF

4: Ba(OMe)2 / methanol

5: PPTS / acetone

6: DIBAH / CH₂Cl₂ / -78 °C

7: 82 percent

8: 1) Dowex 50W 2) pyridine, DMAP / 1) H₂O

With pyridine; dmap; ruthenium trichloride; sodium periodate; thionyl chloride; N-methyl-2-indolinone; Dowex 50W; sulfuric acid; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; barium methoxide; triethylamine; osmium(VIII) oxide; dihydroquinidine 4-chlorobenzoate; In methanol; dichloromethane; acetone;

DOI:10.1016/S0040-4039(00)97476-8

Reference yield:

(4R,5R)-5-((3aR,4S,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester → Acetic acid (2S,3S,3aR,5S,6R,7R,7aR)-3,5,6-triacetoxy-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-7-yl ester (131121-24-9)

Guidance literature:

Multi-step reaction with 3 steps

1: DIBAH / CH₂Cl₂ / -78 °C

2: 82 percent

3: 1) Dowex 50W 2) pyridine, DMAP / 1) H₂O

With pyridine; dmap; Dowex 50W; diisobutylaluminium hydride; In dichloromethane;

DOI:10.1016/S0040-4039(00)97476-8

upstream raw materials:

acetic anhydride

(E)-1-Benzyloxy-4-[(4S,5S)-5-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-but-3-en-2-one

(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde

(E)-ethyl 3-((3aR,4R,6R,6aR)-tetrahydro-4-methoxy-2,2-dimethylfuro[3,4-d][1,3]dioxol-6-yl)acrylate

Downstream raw materials:

Acetic acid (2S,3S,3aR,5S,6S,7R,7aR)-3,6-diacetoxy-5-allyl-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-7-yl ester

(E)-5-[(3S,3aR,5S,6S,7R,7aR)-3,6,7-Triacetoxy-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-5-yl]-pent-2-enoic acid ethyl ester

Acetic acid (2S,3S,3aR,5S,6S,7R,7aR)-3,6-diacetoxy-2-(3-benzyloxy-2-oxo-propyl)-5-(3-hydroxy-propyl)-hexahydro-furo[3,2-b]pyran-7-yl ester

C₂₃H₂₈O₈

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