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

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Chemical Name: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
CAS No.:65011-75-8
Molecular Formula:C₃₈H₄₈O₇Si
Molecular Weight:644.88
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 13 articles about 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 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: 89.0%

: 98-88-4
benzoyl chloride

: 65011-74-7
(Z)-7-[(2S,3S,4S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl]-hept-5-enoic acid methyl ester

: 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

Guidance literature:: With pyridine; 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

: 65011-75-8
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

Guidance literature:: Multi-step reaction with 6 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

With pyridine; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; potassium carbonate; lithium hexamethyldisilazane; palladium hydroxide - carbon; In 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

: 65011-75-8
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

Guidance literature:: Multi-step reaction with 7 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

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