Benzoic acid (2S,3S,4R,6R)-3-allyloxy-6-((3aS,6R,6aR)-6-methoxy-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-3a-ylmethoxy)-2-methyl-5-oxo-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Benzoic acid (2S,3S,4R,6R)-3-allyloxy-6-((3aS,6R,6aR)-6-methoxy-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-3a-ylmethoxy)-2-methyl-5-oxo-tetrahydro-pyran-4-yl ester
• CAS No.: 1053638-27-9
• Molecular Formula: C₂₅H₃₂O₁₀
• Molecular Weight: 492.523

Synonyms:

Chemical Property of Benzoic acid (2S,3S,4R,6R)-3-allyloxy-6-((3aS,6R,6aR)-6-methoxy-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-3a-ylmethoxy)-2-methyl-5-oxo-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of Benzoic acid (2S,3S,4R,6R)-3-allyloxy-6-((3aS,6R,6aR)-6-methoxy-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-3a-ylmethoxy)-2-methyl-5-oxo-tetrahydro-pyran-4-yl ester

There total 6 articles about Benzoic acid (2S,3S,4R,6R)-3-allyloxy-6-((3aS,6R,6aR)-6-methoxy-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-3a-ylmethoxy)-2-methyl-5-oxo-tetrahydro-pyran-4-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:

methyl 2,3-O-isopropylidene-3-C-(hydroxymethyl)-α-D-erythrofuranoside (24679-88-7) + ethyl 4-O-allyl-3-O-benzoyl-1-thio-α-L-rhamnopyranosid-2-ulose (335591-36-1) → Benzoic acid (2S,3S,4R,6R)-3-allyloxy-6-((3aS,6R,6aR)-6-methoxy-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-3a-ylmethoxy)-2-methyl-5-oxo-tetrahydro-pyran-4-yl ester (1053638-27-9)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at 20 ℃; for 0.75h;

DOI:10.1016/S0008-6215(00)00316-5

Reference yield:

(3aR,4S,6S,7S,7aR)-4-Ethylsulfanyl-2-methoxy-2,6-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol (162466-36-6) → Benzoic acid (2S,3S,4R,6R)-3-allyloxy-6-((3aS,6R,6aR)-6-methoxy-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-3a-ylmethoxy)-2-methyl-5-oxo-tetrahydro-pyran-4-yl ester (1053638-27-9)

Guidance literature:

Multi-step reaction with 6 steps

1: dimethylformamide / 0.17 h / 0 °C

2: water; acetic acid / 0.5 h / 20 °C

3: 49.8 percent / pyridine / 0.5 h

4: 72.2 percent / HCl / methanol / 8 h / 20 °C

5: 62.2 percent / pyridinium chlorochromate / CH₂Cl₂ / 2.5 h / Heating

6: N-iodosuccinimide; triflic acid; 3A-MS / CH₂Cl₂ / 0.75 h / 20 °C

With pyridine; hydrogenchloride; N-iodo-succinimide; trifluorormethanesulfonic acid; water; acetic acid; pyridinium chlorochromate; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)00316-5

Reference yield:

Acetic acid (2S,3R,4R,5R,6S)-5-allyloxy-2-ethylsulfanyl-4-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester (221366-31-0) → Benzoic acid (2S,3S,4R,6R)-3-allyloxy-6-((3aS,6R,6aR)-6-methoxy-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-3a-ylmethoxy)-2-methyl-5-oxo-tetrahydro-pyran-4-yl ester (1053638-27-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 49.8 percent / pyridine / 0.5 h

2: 72.2 percent / HCl / methanol / 8 h / 20 °C

3: 62.2 percent / pyridinium chlorochromate / CH₂Cl₂ / 2.5 h / Heating

4: N-iodosuccinimide; triflic acid; 3A-MS / CH₂Cl₂ / 0.75 h / 20 °C

With pyridine; hydrogenchloride; N-iodo-succinimide; trifluorormethanesulfonic acid; pyridinium chlorochromate; In methanol; dichloromethane;

DOI:10.1016/S0008-6215(00)00316-5

upstream raw materials:

methyl 2,3-O-isopropylidene-3-C-(hydroxymethyl)-α-D-erythrofuranoside

ethyl 4-O-allyl-3-O-benzoyl-1-thio-α-L-rhamnopyranosid-2-ulose

(3aR,4S,6S,7S,7aR)-4-Ethylsulfanyl-2-methoxy-2,6-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol

(3aR,4S,6S,7S,7aR)-7-Allyloxy-4-ethylsulfanyl-2-methoxy-2,6-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

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