(E)-3-[(2S,3R,4R,5R)-3-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-acrylic acid ethyl ester

Base Information

• Chemical Name: (E)-3-[(2S,3R,4R,5R)-3-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-acrylic acid ethyl ester
• CAS No.: 155369-80-5
• Molecular Formula: C₄₁H₄₈O₇Si
• Molecular Weight: 680.913

Synonyms:(E)-3-[(2S,3R,4R,5R)-3-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-acrylic acid ethyl ester

Chemical Property of (E)-3-[(2S,3R,4R,5R)-3-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-acrylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-[(2S,3R,4R,5R)-3-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-acrylic acid ethyl ester

There total 15 articles about (E)-3-[(2S,3R,4R,5R)-3-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-acrylic 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) → (E)-3-[(2S,3R,4R,5R)-3-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-acrylic acid ethyl ester (155369-80-5)

Guidance literature:

Multi-step reaction with 14 steps

1: 93 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

2: 76 percent / 6 N aq. HCl / tetrahydrofuran / 5 h / Heating

3: 55 percent / ZnCl₂ / acetonitrile / 6.5 h / 60 °C

4: 85 percent / dl-CSA / CH₂Cl₂ / 1 h / Ambient temperature

5: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h

6: 97 percent / K₂CO₃ / methanol; CH₂Cl₂ / 1 h / 0 °C

7: 87 percent / t-BuOK / tetrahydrofuran / 0.5 h / Ambient temperature

8: 84 percent / 80percent AcOH / CH₂Cl₂ / 96 h / Ambient temperature

9: 94 percent / Et₃N, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

10: 1.) NaH / 1.) THF, DMSO, RT, 2.) THF, DMSO, RT, 3 h

11: 100 percent / dl-CSA / methanol; CH₂Cl₂ / 12 h / Ambient temperature

12: 93 percent / imidazole / CH₂Cl₂ / 0.75 h / Ambient temperature

13: HgO, BF₃*Et₂O / tetrahydrofuran; H₂O / 1.5 h / 60 °C

14: 1.) tert-BuOK / 1.) THF, RT, 30 min, 2.) THF, 30 min

With pyridine; 1H-imidazole; hydrogenchloride; dmap; DL-10-camphorsulfonic acid; boron trifluoride diethyl etherate; potassium tert-butylate; sodium hydride; potassium carbonate; acetic acid; triethylamine; mercury(II) oxide; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;

DOI:10.1248/cpb.45.1265

Reference yield:

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose (18685-18-2) → (E)-3-[(2S,3R,4R,5R)-3-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-acrylic acid ethyl ester (155369-80-5)

Guidance literature:

Multi-step reaction with 15 steps

1: H₂SO₄ / methanol / 0.25 h / Ambient temperature

2: 93 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

3: 76 percent / 6 N aq. HCl / tetrahydrofuran / 5 h / Heating

4: 55 percent / ZnCl₂ / acetonitrile / 6.5 h / 60 °C

5: 85 percent / dl-CSA / CH₂Cl₂ / 1 h / Ambient temperature

6: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h

7: 97 percent / K₂CO₃ / methanol; CH₂Cl₂ / 1 h / 0 °C

8: 87 percent / t-BuOK / tetrahydrofuran / 0.5 h / Ambient temperature

9: 84 percent / 80percent AcOH / CH₂Cl₂ / 96 h / Ambient temperature

10: 94 percent / Et₃N, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

11: 1.) NaH / 1.) THF, DMSO, RT, 2.) THF, DMSO, RT, 3 h

12: 100 percent / dl-CSA / methanol; CH₂Cl₂ / 12 h / Ambient temperature

13: 93 percent / imidazole / CH₂Cl₂ / 0.75 h / Ambient temperature

14: HgO, BF₃*Et₂O / tetrahydrofuran; H₂O / 1.5 h / 60 °C

15: 1.) tert-BuOK / 1.) THF, RT, 30 min, 2.) THF, 30 min

With pyridine; 1H-imidazole; hydrogenchloride; dmap; DL-10-camphorsulfonic acid; sulfuric acid; boron trifluoride diethyl etherate; potassium tert-butylate; sodium hydride; potassium carbonate; acetic acid; triethylamine; mercury(II) oxide; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;

DOI:10.1248/cpb.45.1265

Reference yield:

benzyl chloride (100-44-7) → (E)-3-[(2S,3R,4R,5R)-3-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-acrylic acid ethyl ester (155369-80-5)

Guidance literature:

Multi-step reaction with 16 steps

1: 1.) NaH / 1.) THF, DMSO, RT, 15 min, 2.) THF, DMSO, RT, 35 min

2: H₂SO₄ / methanol / 0.25 h / Ambient temperature

3: 93 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

4: 76 percent / 6 N aq. HCl / tetrahydrofuran / 5 h / Heating

5: 55 percent / ZnCl₂ / acetonitrile / 6.5 h / 60 °C

6: 85 percent / dl-CSA / CH₂Cl₂ / 1 h / Ambient temperature

7: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h

8: 97 percent / K₂CO₃ / methanol; CH₂Cl₂ / 1 h / 0 °C

9: 87 percent / t-BuOK / tetrahydrofuran / 0.5 h / Ambient temperature

10: 84 percent / 80percent AcOH / CH₂Cl₂ / 96 h / Ambient temperature

11: 94 percent / Et₃N, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

12: 1.) NaH / 1.) THF, DMSO, RT, 2.) THF, DMSO, RT, 3 h

13: 100 percent / dl-CSA / methanol; CH₂Cl₂ / 12 h / Ambient temperature

14: 93 percent / imidazole / CH₂Cl₂ / 0.75 h / Ambient temperature

15: HgO, BF₃*Et₂O / tetrahydrofuran; H₂O / 1.5 h / 60 °C

16: 1.) tert-BuOK / 1.) THF, RT, 30 min, 2.) THF, 30 min

With pyridine; 1H-imidazole; hydrogenchloride; dmap; DL-10-camphorsulfonic acid; sulfuric acid; boron trifluoride diethyl etherate; potassium tert-butylate; sodium hydride; potassium carbonate; acetic acid; triethylamine; mercury(II) oxide; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;

DOI:10.1248/cpb.45.1265

upstream raw materials:

(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

benzyl chloride

6-O-Benzoyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose

Downstream raw materials:

(E)-3-[(2S,3R,4R,5R)-3-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-prop-2-en-1-ol

2,2-Dimethyl-propionic acid (4S,5S)-5-((2R,3S,4S,5R)-3-benzyloxy-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

2,2-Dimethyl-propionic acid (4S,5S)-5-((4aR,6R,7R,7aS)-7-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,2-d][1,3]dioxin-6-yl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Toluene-4-sulfonic acid 2-((3aS,4S,5aR,5bS,9aR,10aR,10bR)-2,2,7,7-tetramethyl-octahydro-1,3,5,6,8,10-hexaoxa-cyclopenta[a]fluoren-4-yl)-ethyl ester

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