3-O-benzyl-2-deoxy-D-ribonolactone

Base Information

• Chemical Name: 3-O-benzyl-2-deoxy-D-ribonolactone
• CAS No.: 91879-31-1
• Molecular Formula: C₁₂H₁₄O₄
• Molecular Weight: 222.241
• Mol file: 91879-31-1.mol

Synonyms:3-O-benzyl-2-deoxy-D-ribonolactone

Chemical Property of 3-O-benzyl-2-deoxy-D-ribonolactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-benzyl-2-deoxy-D-ribonolactone

There total 14 articles about 3-O-benzyl-2-deoxy-D-ribonolactone 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: 93.0%

5-O-(tert-butyldiphenylsilyl)-3-O-benzyl-2-deoxy-D-ribonolactone (138433-69-9) → 3-O-benzyl-2-deoxy-D-ribonolactone (91879-31-1)

Guidance literature:

With pyridine; hydrogen fluoride; In tetrahydrofuran; at 0 - 5 ℃; for 4h;

Reference yield:

(E)-5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-en-1-ol (127665-77-4) → 3-O-benzyl-2-deoxy-D-ribonolactone (91879-31-1)

Guidance literature:

Multi-step reaction with 6 steps

1: L-(-)-diethyl tartrate; Ti(iPrO)4; TBHP / 4 Angstroem molecular sieves

2: Ti(iPrO)4 / toluene / 72 h / Heating

3: p-toluenesulfonic acid / CH₂Cl₂ / 0.5 h

4: 1.2 g / TBAF / tetrahydrofuran

5: CrO₃ / acetone / 0 °C

6: camphor sulfonic acid / CH₂Cl₂; methanol

With chromium(VI) oxide; titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(-)-diethyl tartrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; 4 A molecular sieve; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; 1: Sharpless asymmetric epoxidation;

DOI:10.1021/jm034216y

Reference yield:

methyl 5-(tert-butyldiphenylsilyl)oxy-2-pentenoate (162473-68-9) → 3-O-benzyl-2-deoxy-D-ribonolactone (91879-31-1)

Guidance literature:

Multi-step reaction with 7 steps

1: DIBAL-H / CH₂Cl₂; cyclohexane / 0.5 h / -78 - 20 °C

2: L-(-)-diethyl tartrate; Ti(iPrO)4; TBHP / 4 Angstroem molecular sieves

3: Ti(iPrO)4 / toluene / 72 h / Heating

4: p-toluenesulfonic acid / CH₂Cl₂ / 0.5 h

5: 1.2 g / TBAF / tetrahydrofuran

6: CrO₃ / acetone / 0 °C

7: camphor sulfonic acid / CH₂Cl₂; methanol

With chromium(VI) oxide; titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(-)-diethyl tartrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4 A molecular sieve; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; acetone; toluene; 2: Sharpless asymmetric epoxidation;

DOI:10.1021/jm034216y

upstream raw materials:

5-O-(tert-butyldiphenylsilyl)-3-O-benzyl-2-deoxy-D-ribonolactone

(E)-5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-en-1-ol

(2S,3S)-(3-(2-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)ethyl)-2-oxiranyl)methan-1-ol

methyl 5-(tert-butyldiphenylsilyl)oxy-2-pentenoate

Downstream raw materials:

2-deoxy-D-ribonolactone

5-O-tetradecanoyl-3-O-benzyl-2-deoxy-D-ribonolactone

Refernces

• 1、 Teng, Kelly,Marquez, Victor E.,Milne, George W. A.,Barchi Jr., Joseph J.,Kazanietz, Marcelo G.,Lewin, Nancy E.,Blumberg, Peter M.,Abushanab, Elie. "Conformationally constrained analogues of diacylglycerol. Interaction of γ-lactones with the phorbol ester receptor of protein kinase C". . p. 1059 - 1070. Retrieved 2007/10/02.