Acetic acid (2R,3R,4S,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-2-(2,4-diiodo-5,6-dimethoxy-3-methyl-phenoxy)-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-2-(2,4-diiodo-5,6-dimethoxy-3-methyl-phenoxy)-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 138785-35-0
• Molecular Formula: C₂₄H₃₈I₂O₈Si
• Molecular Weight: 736.455

Synonyms:Acetic acid (2R,3R,4S,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-2-(2,4-diiodo-5,6-dimethoxy-3-methyl-phenoxy)-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3R,4S,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-2-(2,4-diiodo-5,6-dimethoxy-3-methyl-phenoxy)-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of Acetic acid (2R,3R,4S,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-2-(2,4-diiodo-5,6-dimethoxy-3-methyl-phenoxy)-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester

There total 22 articles about Acetic acid (2R,3R,4S,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-2-(2,4-diiodo-5,6-dimethoxy-3-methyl-phenoxy)-4-methoxy-6-methyl-tetrahydro-pyran-3-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%

5-hydroxy-2,6-diiodo-3,4-dimethoxytoluene (115592-76-2) + 2-O-acetyl-6-deoxy-4-O-<(1,1-dimethylethyl)dimethylsilyl>-3-O-methyl-L-mannopyranosyl trichloracetimidate → 4,6-diiodo-2,3-dimethoxy-5-methylphenyl 2-O-acetyl-6-deoxy-4-O-<(1,1-dimethylethyl)dimethylsilyl>-3-O-methyl-α-L-mannopyranoside (138785-35-0)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -48 ℃; for 0.5h;

DOI:10.1021/ja00126a013

Reference yield: 89.0%

5-hydroxy-2,6-diiodo-3,4-dimethoxytoluene (115592-76-2) + Acetic acid (2S,3R,4S,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-6-methyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester (138785-31-6) → 4,6-diiodo-2,3-dimethoxy-5-methylphenyl 2-O-acetyl-6-deoxy-4-O-<(1,1-dimethylethyl)dimethylsilyl>-3-O-methyl-α-L-mannopyranoside (138785-35-0) + Acetic acid (2R,3R,4S,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-2-(2,4-diiodo-5,6-dimethoxy-3-methyl-phenoxy)-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester (138785-35-0)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -48 ℃; Yields of byproduct given;

Reference yield: 89.0%

5-hydroxy-2,6-diiodo-3,4-dimethoxytoluene (115592-76-2) + Acetic acid (2S,3R,4S,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-6-methyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester (138785-31-6) → 4,6-diiodo-2,3-dimethoxy-5-methylphenyl 2-O-acetyl-6-deoxy-4-O-<(1,1-dimethylethyl)dimethylsilyl>-3-O-methyl-α-L-mannopyranoside (138785-35-0) + Acetic acid (2R,3R,4S,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-2-(2,4-diiodo-5,6-dimethoxy-3-methyl-phenoxy)-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester (138785-35-0)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -48 ℃; Yields of byproduct given;

upstream raw materials:

5-hydroxy-2,6-diiodo-3,4-dimethoxytoluene

Acetic acid (2S,3R,4S,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-6-methyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

tert-butyldimethylsilyl chloride

Benzyl-2,3,6-tridesoxy-α-L-erythro-hex-2-enopyranosid

Downstream raw materials:

4,6-diiodo-2,3-dimethoxy-5-methylphenyl 6-deoxy-2,4-O,O-bis<(1,1-dimethylethyl)dimethylsilyl>-3-O-methyl-α-L-mannopyranoside

4-hydroxymethyl-6-iodo-2,3-dimethoxy-5-methylphenyl 6-deoxy-2,4-O,O-bis<(1,1-dimethylethyl)dimethylsilyl>-3-O-methyl-α-L-mannopyranoside

4-<(6-deoxy-2,4-O,O-bis<(1,1-dimethylethyl)dimethylsilyl>-3-O-methyl-α-L-mannopyranosyl)oxy>-5-iodo-2,3-dimethoxy-6-methylbenzaldehyde

2-[(2S,3R,4R,5S,6S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-6-methyl-tetrahydro-pyran-2-yloxy]-5-iodo-3,4-dimethoxy-6-methyl-benzoic acid methyl ester

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