1'-deoxy-1'-β-(5-phenylnaphth-1-yl)-3',5'-bis-O-tert-butyldimethylsilyl-2'-O-thionocarbonylimidazolyl-arabinose

Base Information

• Chemical Name: 1'-deoxy-1'-β-(5-phenylnaphth-1-yl)-3',5'-bis-O-tert-butyldimethylsilyl-2'-O-thionocarbonylimidazolyl-arabinose
• CAS No.: 911836-29-8
• Molecular Formula: C₃₇H₅₀N₂O₄SSi₂
• Molecular Weight: 675.052

Synonyms:1'-deoxy-1'-β-(5-phenylnaphth-1-yl)-3',5'-bis-O-tert-butyldimethylsilyl-2'-O-thionocarbonylimidazolyl-arabinose

Chemical Property of 1'-deoxy-1'-β-(5-phenylnaphth-1-yl)-3',5'-bis-O-tert-butyldimethylsilyl-2'-O-thionocarbonylimidazolyl-arabinose

Chemical Property:

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Technology Process of 1'-deoxy-1'-β-(5-phenylnaphth-1-yl)-3',5'-bis-O-tert-butyldimethylsilyl-2'-O-thionocarbonylimidazolyl-arabinose

There total 7 articles about 1'-deoxy-1'-β-(5-phenylnaphth-1-yl)-3',5'-bis-O-tert-butyldimethylsilyl-2'-O-thionocarbonylimidazolyl-arabinose 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: 80.0%

1'-deoxy-1'-β-(5-phenylnaphth-1-yl)-3',5'-bis-O-tert-butyldimethylsilyl-arabinose (911836-25-4) + 1,1'-Thiocarbonyldiimidazole (6160-65-2) → 1'-deoxy-1'-β-(5-phenylnaphth-1-yl)-3',5'-bis-O-tert-butyldimethylsilyl-2'-O-thionocarbonylimidazolyl-arabinose (911836-29-8)

Guidance literature:

In dichloromethane; for 24h;

DOI:10.1021/ol061701p

Reference yield:

1-bromo-5-phenylnaphthalene (911836-38-9) → 1'-deoxy-1'-β-(5-phenylnaphth-1-yl)-3',5'-bis-O-tert-butyldimethylsilyl-2'-O-thionocarbonylimidazolyl-arabinose (911836-29-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: magnesium; iodine / tetrahydrofuran / 40 °C

1.2: aluminum chloride / tetrahydrofuran / 2 h / 20 °C

1.3: 147 mg / tetrahydrofuran; CH₂Cl₂ / 3 h / cooling

2.1: 80 percent / CH₂Cl₂ / 24 h

With iodine; magnesium; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol061701p

Reference yield:

5-bromo-1-phenyl-1,2,3,4-tetrahydro-naphthalen-1-ol (911836-37-8) → 1'-deoxy-1'-β-(5-phenylnaphth-1-yl)-3',5'-bis-O-tert-butyldimethylsilyl-2'-O-thionocarbonylimidazolyl-arabinose (911836-29-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 50 mg / TFA; triphenylmethanol / 48 h

2.1: magnesium; iodine / tetrahydrofuran / 40 °C

2.2: aluminum chloride / tetrahydrofuran / 2 h / 20 °C

2.3: 147 mg / tetrahydrofuran; CH₂Cl₂ / 3 h / cooling

3.1: 80 percent / CH₂Cl₂ / 24 h

With triphenylmethyl alcohol; iodine; magnesium; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol061701p

upstream raw materials:

1'-deoxy-1'-β-(5-phenylnaphth-1-yl)-3',5'-bis-O-tert-butyldimethylsilyl-arabinose

1,1'-Thiocarbonyldiimidazole

1-bromo-5-phenylnaphthalene

5-bromo-1-phenyl-1,2,3,4-tetrahydro-naphthalen-1-ol

Downstream raw materials:

1',2'-dideoxy-1'-β-(5-phenylnaphth-1-yl)-3',5'-bis-O-tert-butyldimethylsilyl-ribose

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