1,5-anhydro-3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-2-nitro-D-lyxo-hex-1-enitol

Base Information

• Chemical Name: 1,5-anhydro-3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-2-nitro-D-lyxo-hex-1-enitol
• CAS No.: 365455-25-0
• Molecular Formula: C₃₆H₃₉NO₆Si
• Molecular Weight: 609.794

Synonyms:1,5-anhydro-3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-2-nitro-D-lyxo-hex-1-enitol

Chemical Property of 1,5-anhydro-3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-2-nitro-D-lyxo-hex-1-enitol

Chemical Property:

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Technology Process of 1,5-anhydro-3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-2-nitro-D-lyxo-hex-1-enitol

There total 4 articles about 1,5-anhydro-3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-2-nitro-D-lyxo-hex-1-enitol 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: 84.0%

3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-D-galactal (201800-34-2) → 1,5-anhydro-3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-2-nitro-D-lyxo-hex-1-enitol (365455-25-0)

Guidance literature:

With nitric acid; acetic anhydride; at -50 - -22 ℃;

DOI:10.1002/ejoc.200390142

Reference yield: 57.6%

→ 1,5-anhydro-3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-2-nitro-D-lyxo-hex-1-enitol (365455-25-0)

Guidance literature:

With 2,6-di-tert-butyl-4-methylpyridine; tetrabutylammonium nitrate; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;

With trifluoromethylsulfonic anhydride; In dichloromethane; at -70 ℃; for 0.0833333h; Inert atmosphere;

Reference yield:

Acetic acid (3R,4R,5R,6R)-4,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-nitro-tetrahydro-pyran-2-yl ester → 1,5-anhydro-3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-2-nitro-D-lyxo-hex-1-enitol (365455-25-0)

Guidance literature:

With triethylamine; In dichloromethane; for 0.333333h;

DOI:10.1002/1521-3773(20010716)40:14<2654::AID-ANIE2654>3.0.CO;2-L

upstream raw materials:

3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-D-galactal

Downstream raw materials:

O-(3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester

O-(3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-2-nitro-α-D-galactopyranosyl)-(1->3)-6-O-(triisopropylsilyl)-D-galactal

N-(9H-fluoren-9-yl)methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonine

N-(tert-butoxycarbonyl)-O-{O-[methyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosyl)onate]-(2->6)-(2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)}-L-threonine tert-butyl ester

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