2-Methyl-propane-2-sulfinic acid {(S)-1-[(2R,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl}-amide

Base Information

• Chemical Name: 2-Methyl-propane-2-sulfinic acid {(S)-1-[(2R,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl}-amide
• CAS No.: 521065-39-4
• Molecular Formula: C₃₁H₄₃N₃O₅SSi
• Molecular Weight: 597.851
• Mol file: 521065-39-4.mol

Synonyms:2-Methyl-propane-2-sulfinic acid {(S)-1-[(2R,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl}-amide

Chemical Property of 2-Methyl-propane-2-sulfinic acid {(S)-1-[(2R,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl}-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Methyl-propane-2-sulfinic acid {(S)-1-[(2R,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl}-amide

There total 7 articles about 2-Methyl-propane-2-sulfinic acid {(S)-1-[(2R,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl}-amide 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: 76.0%

methylmagnesium bromide (75-16-1) + 2-Methyl-propane-2-sulfinic acid 1-[(2R,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-meth-(E)-ylideneamide → 2-Methyl-propane-2-sulfinic acid {(R)-1-[(2R,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl}-amide + 2-Methyl-propane-2-sulfinic acid {(S)-1-[(2R,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl}-amide (521065-39-4)

Guidance literature:

In diethyl ether; at -48 - 20 ℃; Further Variations:; Solvents; Product distribution;

DOI:10.1016/S0040-4039(02)02514-5

Reference yield: 30.0%

methyllithium (917-54-4) + 2-Methyl-propane-2-sulfinic acid 1-[(2R,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-meth-(E)-ylideneamide → 2-Methyl-propane-2-sulfinic acid {(R)-1-[(2R,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl}-amide + 2-Methyl-propane-2-sulfinic acid {(S)-1-[(2R,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl}-amide (521065-39-4)

Guidance literature:

In tetrahydrofuran; at -48 ℃;

DOI:10.1016/S0040-4039(02)02514-5

Reference yield:

1-[(2R,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-trityloxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (83479-97-4) → 2-Methyl-propane-2-sulfinic acid {(S)-1-[(2R,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl}-amide (521065-39-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / AcOH / H₂O

2: 96 percent / DCC; DMSO; TFA*pyridine

3: 74 percent / benzene / Heating; azeotropic distillation

4: 30 percent / tetrahydrofuran / -48 °C

With pyridinium trifluroacetate; acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; In tetrahydrofuran; water; benzene;

DOI:10.1016/S0040-4039(02)02514-5

upstream raw materials:

methyllithium

methylmagnesium bromide

1-[(2R,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-trityloxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

1-[(2R,4S,5R)-4-(tert-butyldiphenylsilanyloxy)-5-hydroxymethyltetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Downstream raw materials:

1-[(2R,4S,5R)-5-((S)-1-Amino-ethyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione