(2'S,3'R,4'R,5'R,4aS,5aR)-4'-acetoxy-3'-benzyloxy-6-benzyl-5'-(1H,3H-pyrimidyl-2,4-dion-1-yl)-6-aza-3,5-dioxa-bicyclo[4.2.1]nonanespiro[1.2']tetrahydro-furan

Base Information

• Chemical Name: (2'S,3'R,4'R,5'R,4aS,5aR)-4'-acetoxy-3'-benzyloxy-6-benzyl-5'-(1H,3H-pyrimidyl-2,4-dion-1-yl)-6-aza-3,5-dioxa-bicyclo[4.2.1]nonanespiro[1.2']tetrahydro-furan
• CAS No.: 952716-12-0
• Molecular Formula: C₂₉H₃₁N₃O₈
• Molecular Weight: 549.58
• Mol file: 952716-12-0.mol

Synonyms:

Chemical Property of (2'S,3'R,4'R,5'R,4aS,5aR)-4'-acetoxy-3'-benzyloxy-6-benzyl-5'-(1H,3H-pyrimidyl-2,4-dion-1-yl)-6-aza-3,5-dioxa-bicyclo[4.2.1]nonanespiro[1.2']tetrahydro-furan

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2'S,3'R,4'R,5'R,4aS,5aR)-4'-acetoxy-3'-benzyloxy-6-benzyl-5'-(1H,3H-pyrimidyl-2,4-dion-1-yl)-6-aza-3,5-dioxa-bicyclo[4.2.1]nonanespiro[1.2']tetrahydro-furan

There total 9 articles about (2'S,3'R,4'R,5'R,4aS,5aR)-4'-acetoxy-3'-benzyloxy-6-benzyl-5'-(1H,3H-pyrimidyl-2,4-dion-1-yl)-6-aza-3,5-dioxa-bicyclo[4.2.1]nonanespiro[1.2']tetrahydro-furan 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:

C27H31NO8 + O,O'-bis-(trimethylsilyl)uracil (10457-14-4) → (2'S,3'R,4'R,5'R,4aS,5aR)-4'-acetoxy-3'-benzyloxy-6-benzyl-5'-(1H,3H-pyrimidyl-2,4-dion-1-yl)-6-aza-3,5-dioxa-bicyclo[4.2.1]nonanespiro[1.2']tetrahydro-furan (952716-12-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 20 ℃; for 5h;

DOI:10.1021/jo070846m

Reference yield:

(3aR,4aR,5R,6R)-[6-benzyloxy-5-(tert-butyldimethylsilanyloxymethyl)-2,2-dimethyltetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-methanol (952716-08-4) → (2'S,3'R,4'R,5'R,4aS,5aR)-4'-acetoxy-3'-benzyloxy-6-benzyl-5'-(1H,3H-pyrimidyl-2,4-dion-1-yl)-6-aza-3,5-dioxa-bicyclo[4.2.1]nonanespiro[1.2']tetrahydro-furan (952716-12-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 83 percent / NaH / tetrahydrofuran / 4.5 h / Heating

2: 75 percent / TBAF / tetrahydrofuran / 24 h / 20 °C

3: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -60 - 20 °C

4: 600 mg / ethanol / 26 h

5: sulfuric acid / acetonitrile; H₂O / 12 h / 20 °C

6: pyridine / 15 h / 20 °C

7: 191 mg / TMSOTf / 1,2-dichloro-ethane / 5 h / 20 °C

With pyridine; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; tetrabutyl ammonium fluoride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile; 3: Swern oxidation / 7: Vorbrueggen reaction;

DOI:10.1021/jo070846m

Reference yield:

(3aR,4aR,5R,6R)-5-allyloxymethyl-6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-ylmethoxy-tert-butyl-dimethyl-silane (952716-09-5) → (2'S,3'R,4'R,5'R,4aS,5aR)-4'-acetoxy-3'-benzyloxy-6-benzyl-5'-(1H,3H-pyrimidyl-2,4-dion-1-yl)-6-aza-3,5-dioxa-bicyclo[4.2.1]nonanespiro[1.2']tetrahydro-furan (952716-12-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 75 percent / TBAF / tetrahydrofuran / 24 h / 20 °C

2: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -60 - 20 °C

3: 600 mg / ethanol / 26 h

4: sulfuric acid / acetonitrile; H₂O / 12 h / 20 °C

5: pyridine / 15 h / 20 °C

6: 191 mg / TMSOTf / 1,2-dichloro-ethane / 5 h / 20 °C

With pyridine; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile; 2: Swern oxidation / 6: Vorbrueggen reaction;

DOI:10.1021/jo070846m

upstream raw materials:

O,O'-bis-(trimethylsilyl)uracil

(3aR,4aR,5R,6R)-[6-benzyloxy-5-(tert-butyldimethylsilanyloxymethyl)-2,2-dimethyltetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-methanol

(3aR,4aR,5R,6R)-5-allyloxymethyl-6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-ylmethoxy-tert-butyl-dimethyl-silane

(3aR,4aR,5R,6R)-(5-allyloxymethyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-methanol