(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
Hs Code.:

(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

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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

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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

: 10457-14-4
O,O'-bis-(trimethylsilyl)uracil

: 952716-12-0
(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

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 20 ℃; for 5h;
DOI:10.1021/jo070846m

Reference yield:

: 952716-08-4
(3aR,4aR,5R,6R)-[6-benzyloxy-5-(tert-butyldimethylsilanyloxymethyl)-2,2-dimethyltetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-methanol

: 952716-12-0
(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

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:

: 952716-09-5
(3aR,4aR,5R,6R)-5-allyloxymethyl-6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-ylmethoxy-tert-butyl-dimethyl-silane

: 952716-12-0
(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

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