1-<5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-1-phenyl-D-ribofuranosyl>thymine

Base Information

• Chemical Name: 1-<5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-1-phenyl-D-ribofuranosyl>thymine
• CAS No.: 160053-49-6
• Molecular Formula: C₃₅H₄₀N₂O₆Si
• Molecular Weight: 612.798

Synonyms:1-<5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-1-phenyl-D-ribofuranosyl>thymine

Chemical Property of 1-<5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-1-phenyl-D-ribofuranosyl>thymine

Chemical Property:

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Technology Process of 1-<5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-1-phenyl-D-ribofuranosyl>thymine

There total 5 articles about 1-<5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-1-phenyl-D-ribofuranosyl>thymine 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: 31.0%

thymin (65-71-4,28806-14-6,691841-57-3) + 5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-1-phenyl-D-ribofuranose (174590-90-0) → 1-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-1-phenyl-βD-ribofuranosyl]thymine (1004554-92-0) + 1-<5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-1-phenyl-D-ribofuranosyl>thymine (160053-49-6)

Guidance literature:

With benzenesulfonamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 50 ℃; for 4.5h;

DOI:10.1016/S0385-5414(07)81201-9

Reference yield:

2,3-O-isopropylidene-D-ribonic-γ-lactone (30725-00-9) → 1-<5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-1-phenyl-D-ribofuranosyl>thymine (160053-49-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / pyridine / 27 h / Ambient temperature

2: 1.) THF, -78 - -30 deg C, 20 min, 2.) -78 - -30 deg C, 30 min

3: 1.) BSA, 2.) TMSOTf / 1.) MeCN, room temperature, 1.5 h, 2.) 0 deg C, 3.5 h

With benzenesulfonamide; trimethylsilyl trifluoromethanesulfonate; In pyridine;

DOI:10.1080/15257779408013242

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 1-<5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-1-phenyl-D-ribofuranosyl>thymine (160053-49-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / pyridine / 27 h / Ambient temperature

2: 1.) THF, -78 - -30 deg C, 20 min, 2.) -78 - -30 deg C, 30 min

3: 1.) BSA, 2.) TMSOTf / 1.) MeCN, room temperature, 1.5 h, 2.) 0 deg C, 3.5 h

With benzenesulfonamide; trimethylsilyl trifluoromethanesulfonate; In pyridine;

DOI:10.1080/15257779408013242

upstream raw materials:

thymin

2,3-O-isopropylidene-D-ribonic-γ-lactone

5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone

tert-butylchlorodiphenylsilane

Downstream raw materials:

1-<2,3-O-isopropylidene-1-phenyl-α-D-ribofuranosyl>thymine

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