1,4-anhydro-2-deoxy-3-O-(diphenoxyphosphoryl)-D-erythro-pentitol 5-[1,4-anhydro-2-deoxy-5-O-(tert-butyldimethylsilyl)-D-erythro-pentit-3-yl 2,2,2-trichloroethyl phosphate]

Base Information

• Chemical Name: 1,4-anhydro-2-deoxy-3-O-(diphenoxyphosphoryl)-D-erythro-pentitol 5-[1,4-anhydro-2-deoxy-5-O-(tert-butyldimethylsilyl)-D-erythro-pentit-3-yl 2,2,2-trichloroethyl phosphate]
• CAS No.: 194724-19-1
• Molecular Formula: C₃₀H₄₃Cl₃O₁₁P₂Si
• Molecular Weight: 776.057
• Mol file: 194724-19-1.mol

Synonyms:

Chemical Property of 1,4-anhydro-2-deoxy-3-O-(diphenoxyphosphoryl)-D-erythro-pentitol 5-[1,4-anhydro-2-deoxy-5-O-(tert-butyldimethylsilyl)-D-erythro-pentit-3-yl 2,2,2-trichloroethyl phosphate]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,4-anhydro-2-deoxy-3-O-(diphenoxyphosphoryl)-D-erythro-pentitol 5-[1,4-anhydro-2-deoxy-5-O-(tert-butyldimethylsilyl)-D-erythro-pentit-3-yl 2,2,2-trichloroethyl phosphate]

There total 9 articles about 1,4-anhydro-2-deoxy-3-O-(diphenoxyphosphoryl)-D-erythro-pentitol 5-[1,4-anhydro-2-deoxy-5-O-(tert-butyldimethylsilyl)-D-erythro-pentit-3-yl 2,2,2-trichloroethyl phosphate] 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:

Phosphoric acid (2R,3S)-2-[[(2R,3S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yloxy]-(2,2,2-trichloro-ethoxy)-phosphanyloxymethyl]-tetrahydro-furan-3-yl ester diphenyl ester → 1,4-anhydro-2-deoxy-3-O-(diphenoxyphosphoryl)-D-erythro-pentitol 5-[1,4-anhydro-2-deoxy-5-O-(tert-butyldimethylsilyl)-D-erythro-pentit-3-yl 2,2,2-trichloroethyl phosphate] (194724-19-1)

Guidance literature:

With 2,3,5-trimethyl-pyridine; iodine; In tetrahydrofuran; water; at -10 ℃; Yield given;

DOI:10.1016/S0040-4020(97)00363-3

Reference yield:

D-2-deoxyribose (452-51-7,13046-70-3,29780-54-9,36792-87-7,36792-88-8,113890-35-0,113890-38-3) → 1,4-anhydro-2-deoxy-3-O-(diphenoxyphosphoryl)-D-erythro-pentitol 5-[1,4-anhydro-2-deoxy-5-O-(tert-butyldimethylsilyl)-D-erythro-pentit-3-yl 2,2,2-trichloroethyl phosphate] (194724-19-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 89 percent / conc. H₂SO₄ / 24 h / 4 °C

2: 1.) BSTFA, 2.) Et₃SiH, TMSOTf / 1.) CH₃CN, 78-80 deg C, 3 h, 2.) overnight, room temperature

3: 76 percent / imidazole / dimethylformamide / 0.17 h / Ambient temperature

4: collidine / tetrahydrofuran / -78 °C

5: tetrahydrofuran / 0.25 h

6: I₂, collidine / tetrahydrofuran; H₂O / -10 °C

With 1H-imidazole; 2,3,5-trimethyl-pyridine; triethylsilane; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; iodine; N,O-Bis(trimethylsilyl)trifluoroacetamide; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(97)00363-3

Reference yield:

(2R,3S)-2-(hydroxymethyl)tetrahydrofuran-3-ol (91547-59-0) → 1,4-anhydro-2-deoxy-3-O-(diphenoxyphosphoryl)-D-erythro-pentitol 5-[1,4-anhydro-2-deoxy-5-O-(tert-butyldimethylsilyl)-D-erythro-pentit-3-yl 2,2,2-trichloroethyl phosphate] (194724-19-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 76 percent / imidazole / dimethylformamide / 0.17 h / Ambient temperature

2: collidine / tetrahydrofuran / -78 °C

3: tetrahydrofuran / 0.25 h

4: I₂, collidine / tetrahydrofuran; H₂O / -10 °C

With 1H-imidazole; 2,3,5-trimethyl-pyridine; iodine; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(97)00363-3

upstream raw materials:

(2R,3S)-2-(hydroxymethyl)tetrahydrofuran-3-ol

D-2-deoxyribose

tert-butyldimethylsilyl chloride

(2R,3S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]tetrahydrofuran-3-ol