methyl 5-O-tert-butyldiphenylsilyl-6,7,8-trideoxy-2,3-O-isopropylidene-α-D-manno-oct-7-ynofuranoside

Base Information

• Chemical Name: methyl 5-O-tert-butyldiphenylsilyl-6,7,8-trideoxy-2,3-O-isopropylidene-α-D-manno-oct-7-ynofuranoside
• CAS No.: 221015-74-3
• Molecular Formula: C₂₈H₃₆O₅Si
• Molecular Weight: 480.676

Synonyms:methyl 5-O-tert-butyldiphenylsilyl-6,7,8-trideoxy-2,3-O-isopropylidene-α-D-manno-oct-7-ynofuranoside

Chemical Property of methyl 5-O-tert-butyldiphenylsilyl-6,7,8-trideoxy-2,3-O-isopropylidene-α-D-manno-oct-7-ynofuranoside

Chemical Property:

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Technology Process of methyl 5-O-tert-butyldiphenylsilyl-6,7,8-trideoxy-2,3-O-isopropylidene-α-D-manno-oct-7-ynofuranoside

There total 2 articles about methyl 5-O-tert-butyldiphenylsilyl-6,7,8-trideoxy-2,3-O-isopropylidene-α-D-manno-oct-7-ynofuranoside 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: 86.0%

tert-butylchlorodiphenylsilane (58479-61-1) + methyl 6,7,8-trideoxy-2,3-O-isopropylidene-α-D-manno-oct-7-ynofuranoside (188640-84-8) → methyl 5-O-tert-butyldiphenylsilyl-6,7,8-trideoxy-2,3-O-isopropylidene-α-D-manno-oct-7-ynofuranoside (221015-74-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 90 ℃; for 12h;

DOI:10.1055/s-1999-3389

Reference yield:

methyl 2,3-O-isopropylidene-α-D-mannofuranoside 5,6-O-cyclic sulfate (127244-81-9) → methyl 5-O-tert-butyldiphenylsilyl-6,7,8-trideoxy-2,3-O-isopropylidene-α-D-manno-oct-7-ynofuranoside (221015-74-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / dimethylformamide; xylene / 0.58 h / -5 °C

2: 86 percent / imidazole / dimethylformamide / 12 h / 90 °C

With 1H-imidazole; In N,N-dimethyl-formamide; xylene;

DOI:10.1055/s-1999-3389

Reference yield: 63.0%

3-O-benzyl 1,2-O-isopropylidene-5,6-O-sulfuryl-α-D-glucofuranose (158946-12-4) + methyl 5-O-tert-butyldiphenylsilyl-6,7,8-trideoxy-2,3-O-isopropylidene-α-D-manno-oct-7-ynofuranoside (221015-74-3) → 6,7,8-trideoxy-3-O-benzyl-1,2-O-isopropylidene-8-(methyl 5-O-tert-butyldiphenylsilyl-6-deoxy-2,3-O-isopropylidene-α-D-manno-furanosid-6-yl)-α-D-gluco-oct-7-ynofuranose (221015-79-8)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; In tetrahydrofuran; at -5 ℃;

DOI:10.1055/s-1999-3389

upstream raw materials:

tert-butylchlorodiphenylsilane

methyl 6,7,8-trideoxy-2,3-O-isopropylidene-α-D-manno-oct-7-ynofuranoside

methyl 2,3-O-isopropylidene-α-D-mannofuranoside 5,6-O-cyclic sulfate

Downstream raw materials:

methyl 6,7,8-trideoxy-2,3-O-isopropylidene-8-(methyl 5-O-tert-butyldiphenylsilyl-6-deoxy-2,3-O-isopropylidene-α-D-manno-furanosid-6-yl)-α-D-manno-oct-7-ynofuranoside

6,7,8-trideoxy-3-O-benzyl-1,2-O-isopropylidene-8-(methyl 5-O-tert-butyldiphenylsilyl-6-deoxy-2,3-O-isopropylidene-α-D-manno-furanosid-6-yl)-α-D-gluco-oct-7-ynofuranose

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