Benzoic acid (2S,3S,4S,6S)-2-hydroxymethyl-6-methoxy-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-pyran-4-yl ester

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Chemical Name:Benzoic acid (2S,3S,4S,6S)-2-hydroxymethyl-6-methoxy-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-pyran-4-yl ester
CAS No.:65011-76-9
Molecular Formula:C₂₂H₃₀O₇
Molecular Weight:406.476
Hs Code.:

Synonyms:Benzoic acid (2S,3S,4S,6S)-2-hydroxymethyl-6-methoxy-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-pyran-4-yl ester

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Chemical Property of Benzoic acid (2S,3S,4S,6S)-2-hydroxymethyl-6-methoxy-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-pyran-4-yl ester

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Technology Process of Benzoic acid (2S,3S,4S,6S)-2-hydroxymethyl-6-methoxy-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-pyran-4-yl ester

There total 16 articles about Benzoic acid (2S,3S,4S,6S)-2-hydroxymethyl-6-methoxy-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-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: 89.5%

: 65011-75-8
Benzoic acid (2S,3S,4S,6S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methoxy-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-pyran-4-yl ester

: 65011-76-9
Benzoic acid (2S,3S,4S,6S)-2-hydroxymethyl-6-methoxy-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-pyran-4-yl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 3h; Ambient temperature;
DOI:10.1139/v81-126

Reference yield:

: 65011-68-9
methyl 3-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-erythro-hexopyranosid-4-ulose

: 65011-76-9
Benzoic acid (2S,3S,4S,6S)-2-hydroxymethyl-6-methoxy-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 48.6 percent / potassium tert-butoxide / toluene / 8 h / Ambient temperature

2: 92 percent / H₂ / 20percent palladium hydroxide on charcoal / methanol; ethyl acetate / 24 h

3: 85 percent / potassium carbonate / methanol / 60 h

4: DIBAH / toluene / 0.5 h / -78 °C

5: 1.) lithium bis(trimethylsilyl)amide / 1.) HMPT, 20 min, room temperature; 2.) CH₂Cl₂/methanol/ether

6: 89 percent / pyridine / Ambient temperature

7: 89.5 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature

With pyridine; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; potassium carbonate; lithium hexamethyldisilazane; palladium hydroxide - carbon; In tetrahydrofuran; methanol; ethyl acetate; toluene;
DOI:10.1139/v81-126

Reference yield:

: 65011-67-8
methyl 3-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-ribo-hexopyranoside

: 65011-76-9
Benzoic acid (2S,3S,4S,6S)-2-hydroxymethyl-6-methoxy-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 94 percent / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, pyridine, trifluoroacetic acid / dimethylsulfoxide

2: 48.6 percent / potassium tert-butoxide / toluene / 8 h / Ambient temperature

3: 92 percent / H₂ / 20percent palladium hydroxide on charcoal / methanol; ethyl acetate / 24 h

4: 85 percent / potassium carbonate / methanol / 60 h

5: DIBAH / toluene / 0.5 h / -78 °C

6: 1.) lithium bis(trimethylsilyl)amide / 1.) HMPT, 20 min, room temperature; 2.) CH₂Cl₂/methanol/ether

7: 89 percent / pyridine / Ambient temperature

8: 89.5 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature

With pyridine; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; lithium hexamethyldisilazane; palladium hydroxide - carbon; In tetrahydrofuran; methanol; dimethyl sulfoxide; ethyl acetate; toluene;
DOI:10.1139/v81-126