{(4S,6R)-2-methoxy-6-[(2-methyl-1-benzofuran-4-yl)methyl]-tetrahydro-2H-pyran-4-yloxy}(tert-butyl)diphenylsilane

Base Information

• Chemical Name: {(4S,6R)-2-methoxy-6-[(2-methyl-1-benzofuran-4-yl)methyl]-tetrahydro-2H-pyran-4-yloxy}(tert-butyl)diphenylsilane
• CAS No.: 529488-06-0
• Molecular Formula: C₃₂H₃₈O₄Si
• Molecular Weight: 514.737

Synonyms:{(4S,6R)-2-methoxy-6-[(2-methyl-1-benzofuran-4-yl)methyl]-tetrahydro-2H-pyran-4-yloxy}(tert-butyl)diphenylsilane

Chemical Property of {(4S,6R)-2-methoxy-6-[(2-methyl-1-benzofuran-4-yl)methyl]-tetrahydro-2H-pyran-4-yloxy}(tert-butyl)diphenylsilane

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Technology Process of {(4S,6R)-2-methoxy-6-[(2-methyl-1-benzofuran-4-yl)methyl]-tetrahydro-2H-pyran-4-yloxy}(tert-butyl)diphenylsilane

There total 2 articles about {(4S,6R)-2-methoxy-6-[(2-methyl-1-benzofuran-4-yl)methyl]-tetrahydro-2H-pyran-4-yloxy}(tert-butyl)diphenylsilane 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: 59.0%

4-bromo-2-methylbenzofuran (219739-70-5) + Trifluoro-methanesulfonic acid (2S,4S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (529488-04-8) → {(4S,6R)-2-methoxy-6-[(2-methyl-1-benzofuran-4-yl)methyl]-tetrahydro-2H-pyran-4-yloxy}(tert-butyl)diphenylsilane (529488-06-0)

Guidance literature:

4-bromo-2-methylbenzofuran; With iodine; magnesium; In tetrahydrofuran; at 20 ℃; for 1h;

Trifluoro-methanesulfonic acid (2S,4S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester; With copper(I) bromide; In tetrahydrofuran; at 0 ℃; for 14h; Further stages.;

DOI:10.1039/b209637b

Reference yield:

methyl 3-O-[tert-butyl-(diphenyl)silyl]-2,4-dideoxy-D-threo-hexopyranoside (530112-01-7) → {(4S,6R)-2-methoxy-6-[(2-methyl-1-benzofuran-4-yl)methyl]-tetrahydro-2H-pyran-4-yloxy}(tert-butyl)diphenylsilane (529488-06-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 96 percent / pyridine / CH₂Cl₂ / 0.25 h / -12 °C

2.1: Mg; I₂ / tetrahydrofuran / 1 h / 20 °C

2.2: 59 percent / CuBr / tetrahydrofuran / 14 h / 0 °C

With pyridine; iodine; magnesium; In tetrahydrofuran; dichloromethane;

DOI:10.1039/b209637b

Reference yield: 84.0%

tert-butylchlorodiphenylsilane (58479-61-1) + allyl-trimethyl-silane (762-72-1) + {(4S,6R)-2-methoxy-6-[(2-methyl-1-benzofuran-4-yl)methyl]-tetrahydro-2H-pyran-4-yloxy}(tert-butyl)diphenylsilane (529488-06-0) → {(2S,4S,6R)-2-allyl-6-[(2-methyl-1-benzofuran-4-yl)methyl]-tetrahydro-2H-pyran-4-yloxy}(tert-butyl)diphenylsilane (529488-09-3)

Guidance literature:

allyl-trimethyl-silane; {(4S,6R)-2-methoxy-6-[(2-methyl-1-benzofuran-4-yl)methyl]-tetrahydro-2H-pyran-4-yloxy}(tert-butyl)diphenylsilane; With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at -25 ℃; for 0.666667h;

tert-butylchlorodiphenylsilane; With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 15h; Further stages.;

DOI:10.1039/b209637b

upstream raw materials:

4-bromo-2-methylbenzofuran

Trifluoro-methanesulfonic acid (2S,4S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

methyl 3-O-[tert-butyl-(diphenyl)silyl]-2,4-dideoxy-D-threo-hexopyranoside

Downstream raw materials:

{(2S,4S,6R)-2-allyl-6-[(2-methyl-1-benzofuran-4-yl)methyl]-tetrahydro-2H-pyran-4-yloxy}(tert-butyl)diphenylsilane

3-{(2R,4S)-4-[tert-butyl(diphenyl)silyloxy]-6-methoxytetrahydro-2H-pyran-2-ylmethyl}-2-formylphenyl acetate

2-(acetyloxy)-6-{(2R,4S)-4-[tert-butyl(diphenyl)silyloxy]-6-methoxytetrahydro-2H-pyran-2-ylmethyl}benzoic acid

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