1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-4-C-methylene-D-erythro-pentitol

Base Information

• Chemical Name: 1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-4-C-methylene-D-erythro-pentitol
• CAS No.: 848862-75-9
• Molecular Formula: C₃₂H₄₀O₄Si
• Molecular Weight: 516.753
• Mol file: 848862-75-9.mol

Synonyms:1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-4-C-methylene-D-erythro-pentitol

Chemical Property of 1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-4-C-methylene-D-erythro-pentitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-4-C-methylene-D-erythro-pentitol

There total 10 articles about 1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-4-C-methylene-D-erythro-pentitol 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: 93.4%

Methyltriphenylphosphonium bromide (1779-49-3) + 1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-4-keto-D-erythro-pentitol (848862-73-7) → 1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-4-C-methylene-D-erythro-pentitol (848862-75-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/ol006999c

Reference yield:

1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-D-ribitol (117174-48-8) → 1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-4-C-methylene-D-erythro-pentitol (848862-75-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 100 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -70 - 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C

2.2: 92 percent / tetrahydrofuran; hexane / 16 h / 20 °C

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1.1: Swern oxidation;

DOI:10.1016/j.tetasy.2004.11.069

Reference yield:

D-Ribose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) → 1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-4-C-methylene-D-erythro-pentitol (848862-75-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: sulfuric acid / 2 h / 20 °C

1.2: 96 percent / acetone / 72 h / 20 °C

2.1: 61 percent / sodium hydride / dimethylformamide / 3 h / 0 °C

3.1: 92 percent / potassium tert-butoxide / dimethylsulfoxide / 16 h / 100 °C

4.1: ozone / CH₂Cl₂ / -78 °C

4.2: 95 percent / triphenylphsphine / CH₂Cl₂ / -78 - 20 °C

5.1: 100 percent / methanol; triethylamine / 16 h / 20 °C

6.1: 88 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 20 °C

7.1: 98 percent / imidazole / dimethylformamide / 16 h / 20 °C

8.1: 100 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -70 - 20 °C

9.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C

9.2: 92 percent / tetrahydrofuran; hexane / 16 h / 20 °C

With 1H-imidazole; methanol; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; sulfuric acid; potassium tert-butylate; sodium hydride; ozone; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 1.2: Fischer glycosidation / 8.1: Swern oxidation;

DOI:10.1016/j.tetasy.2004.11.069

upstream raw materials:

Methyltriphenylphosphonium bromide

1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-4-keto-D-erythro-pentitol

5-O-benzyl-2,3-O-isopropylidene-D-ribitol

5-O-benzyl-2,3-O-isopropylidene-D-ribofuranose

Downstream raw materials:

(2S,3R)-5-benzyl-2,3-O-isopropylidene-4-C-methylene-D-erytho-pentitol

(4R,5R)-5-(1-Benzyloxymethyl-vinyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

(3aR,6aR)-6-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-one

(4R,5S)-(-)-3-[(benzyloxy)methyl]-4,5-O-isopropylidene-2-cyclopenten-1-ol