(1S,3R,4R,7S)-7-(benzyloxy)-1-[(benzyloxy)methyl]-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

Base Information

• Chemical Name: (1S,3R,4R,7S)-7-(benzyloxy)-1-[(benzyloxy)methyl]-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane
• CAS No.: 206055-62-1
• Molecular Formula: C₂₅H₂₆N₂O₆
• Molecular Weight: 450.491
• Mol file: 206055-62-1.mol

Synonyms:(1S,3R,4R,7S)-7-(benzyloxy)-1-[(benzyloxy)methyl]-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

Chemical Property of (1S,3R,4R,7S)-7-(benzyloxy)-1-[(benzyloxy)methyl]-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R,4R,7S)-7-(benzyloxy)-1-[(benzyloxy)methyl]-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

There total 23 articles about (1S,3R,4R,7S)-7-(benzyloxy)-1-[(benzyloxy)methyl]-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 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: 92.0%

1-(3,5-di-O-benzyl-4-C-(p-toluenesulphonyloxymethyl)-α-D-ribofuranosyl)thymine (209968-88-7) → (1S,3R,4R,7S)-7-(benzyloxy)-1-[(benzyloxy)methyl]-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (206055-62-1)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 37h;

DOI:10.1016/S0040-4039(98)00706-0

Reference yield: 86.0%

1-{2-O-acetyl-3-O-benzyl-4-[(benzyloxy)methyl]-5-O-(methylsulfonyl)-α-L-lyxofuranosyl}-5-methylpyrimidine-2,4-(1H,3H)-dione (263547-06-4) → (1S,3R,4R,7S)-7-(benzyloxy)-1-[(benzyloxy)methyl]-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (206055-62-1)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran;

DOI:10.1002/(SICI)1522-2675(20000119)83:1<128::AID-HLCA128>3.0.CO;2-Q

Reference yield: 61.0%

thymin (65-71-4,28806-14-6,691841-57-3) + (1S,3S,4R,7S)-7-Benzyloxy-1-benzyloxymethyl-3-phenylsulfanyl-2,5-dioxa-bicyclo[2.2.1]heptane (219854-48-5) → (1S,3R,4R,7S)-7-(benzyloxy)-1-[(benzyloxy)methyl]-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (206055-62-1)

Guidance literature:

With 4 Angstroem MS; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane;

DOI:10.1080/15257779908041546

upstream raw materials:

1-[(2R,3R,4S,5R)-4-benzyloxy-5-(benzyloxymethyl)-3-hydroxy-5-(hydroxymethyl)tetra-hydrofuran-2-yl]-5-methylpyrimidine-2,4-dione

1-(3,5-di-O-benzyl-4-C-(p-toluenesulphonyloxymethyl)-α-D-ribofuranosyl)thymine

thymin

(1S,3S,4R,7S)-7-Benzyloxy-1-benzyloxymethyl-3-phenylsulfanyl-2,5-dioxa-bicyclo[2.2.1]heptane

Downstream raw materials:

(1S,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

(1S,3S,4R,7S)-7-hydroxy-1-hydroxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

1-[(1R,4R,6R,7S)-4-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptan-6-yl]-5-methylpyrimidine-2,4-dione

(1R,3R,4R,7S)-3-(thymine-1-yl)-1-(4,4′-dimethoxytrityloxy)-7-(2-cyanoethoxy(diisopropylamino)phosphinoxymethyl)-2,5-dioxabicyclo[2.2.1]heptane