(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

Base Information

Chemical Name:(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
CAS No.:65011-74-7
Molecular Formula:C₃₁H₄₄O₆Si
Molecular Weight:540.772
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 12 articles about (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 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: 74.0%

: 78081-19-3
(Z)-7-[(2S,3R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-4-oxo-tetrahydro-pyran-3-yl]-hept-5-enoic acid methyl ester

: 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

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃;
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

: 65011-74-7
(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

Guidance literature:: Multi-step reaction with 5 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

With 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

: 65011-74-7
(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

Guidance literature:: Multi-step reaction with 6 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

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