(R)-((1S,3S,4S,5R,6R)-5-Benzyloxy-3-benzyloxymethyl-6-hydroxy-2,7-dioxa-bicyclo[2.2.1]hept-3-yl)-hydroxy-acetic acid ethyl ester

Base Information

• Chemical Name: (R)-((1S,3S,4S,5R,6R)-5-Benzyloxy-3-benzyloxymethyl-6-hydroxy-2,7-dioxa-bicyclo[2.2.1]hept-3-yl)-hydroxy-acetic acid ethyl ester
• CAS No.: 160906-20-7
• Molecular Formula: C₂₄H₂₈O₈
• Molecular Weight: 444.482
• Mol file: 160906-20-7.mol

Synonyms:

Chemical Property of (R)-((1S,3S,4S,5R,6R)-5-Benzyloxy-3-benzyloxymethyl-6-hydroxy-2,7-dioxa-bicyclo[2.2.1]hept-3-yl)-hydroxy-acetic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-((1S,3S,4S,5R,6R)-5-Benzyloxy-3-benzyloxymethyl-6-hydroxy-2,7-dioxa-bicyclo[2.2.1]hept-3-yl)-hydroxy-acetic acid ethyl ester

There total 7 articles about (R)-((1S,3S,4S,5R,6R)-5-Benzyloxy-3-benzyloxymethyl-6-hydroxy-2,7-dioxa-bicyclo[2.2.1]hept-3-yl)-hydroxy-acetic acid ethyl ester 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:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) → (R)-((1S,3S,4S,5R,6R)-5-Benzyloxy-3-benzyloxymethyl-6-hydroxy-2,7-dioxa-bicyclo[2.2.1]hept-3-yl)-hydroxy-acetic acid ethyl ester (160906-20-7)

Guidance literature:

Multi-step reaction with 6 steps

1: imid / CH₂Cl₂ / 3 h / Ambient temperature

2: DMSO, (COCl)2, Et₃N / biphenyl / 1 h / -78 °C

3: CH₂Cl₂ / 18 h / Ambient temperature

4: Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

5: NaH / tetrahydrofuran / 4 h / Ambient temperature

6: 1.) NMO; 2.) PTSA / 1.) OsO₄ / 1.) CH₃COCH₃, H₂O₂, 8 h; 2.) CHCl₃, ref., 6 h

With 1H-imidazole; N-methyl-2-indolinone; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; osmium(VIII) oxide; In tetrahydrofuran; biphenyl; dichloromethane;

DOI:10.1016/S0040-4039(00)76809-2

Reference yield:

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose (18685-18-2) → (R)-((1S,3S,4S,5R,6R)-5-Benzyloxy-3-benzyloxymethyl-6-hydroxy-2,7-dioxa-bicyclo[2.2.1]hept-3-yl)-hydroxy-acetic acid ethyl ester (160906-20-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 0.8 percent H₂SO₄ / methanol / 12 h / Ambient temperature

2: imid / CH₂Cl₂ / 3 h / Ambient temperature

3: DMSO, (COCl)2, Et₃N / biphenyl / 1 h / -78 °C

4: CH₂Cl₂ / 18 h / Ambient temperature

5: Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

6: NaH / tetrahydrofuran / 4 h / Ambient temperature

7: 1.) NMO; 2.) PTSA / 1.) OsO₄ / 1.) CH₃COCH₃, H₂O₂, 8 h; 2.) CHCl₃, ref., 6 h

With 1H-imidazole; N-methyl-2-indolinone; oxalyl dichloride; sulfuric acid; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; osmium(VIII) oxide; In tetrahydrofuran; methanol; biphenyl; dichloromethane;

DOI:10.1016/S0040-4039(00)76809-2

Reference yield:

3-O-benzyl-6-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D-xylo-hexofuran-5-ulose (106445-05-0) → (R)-((1S,3S,4S,5R,6R)-5-Benzyloxy-3-benzyloxymethyl-6-hydroxy-2,7-dioxa-bicyclo[2.2.1]hept-3-yl)-hydroxy-acetic acid ethyl ester (160906-20-7)

Guidance literature:

Multi-step reaction with 4 steps

1: CH₂Cl₂ / 18 h / Ambient temperature

2: Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

3: NaH / tetrahydrofuran / 4 h / Ambient temperature

4: 1.) NMO; 2.) PTSA / 1.) OsO₄ / 1.) CH₃COCH₃, H₂O₂, 8 h; 2.) CHCl₃, ref., 6 h

With N-methyl-2-indolinone; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; osmium(VIII) oxide; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(00)76809-2

upstream raw materials:

(Z)-4-Benzyloxy-3-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-but-2-enoic acid ethyl ester

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose

1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethanol