Benzoic acid (2R,3S,4R)-4-((4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(2,2-dimethyl-propionyloxymethyl)-5-methoxy-4-methyl-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,4R)-4-((4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(2,2-dimethyl-propionyloxymethyl)-5-methoxy-4-methyl-tetrahydro-furan-3-yl ester
• CAS No.: 129662-87-9
• Molecular Formula: C₃₂H₄₂O₉
• Molecular Weight: 570.68
• Mol file: 129662-87-9.mol

Synonyms:

Chemical Property of Benzoic acid (2R,3S,4R)-4-((4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(2,2-dimethyl-propionyloxymethyl)-5-methoxy-4-methyl-tetrahydro-furan-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,3S,4R)-4-((4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(2,2-dimethyl-propionyloxymethyl)-5-methoxy-4-methyl-tetrahydro-furan-3-yl ester

There total 23 articles about Benzoic acid (2R,3S,4R)-4-((4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(2,2-dimethyl-propionyloxymethyl)-5-methoxy-4-methyl-tetrahydro-furan-3-yl 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:

3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-methyl-3-C-vinyl-α-D-allofuranose (103516-20-7) → Benzoic acid (2R,3S,4R,5R)-4-((4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(2,2-dimethyl-propionyloxymethyl)-5-methoxy-4-methyl-tetrahydro-furan-3-yl ester (129662-87-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 1) ca.3percent O₃ in O₂ 2) Ph₃P / 1) CH₂Cl₂, -78 deg C 2) up to r.t., 1 h

2: 90 percent / benzene / 12 h / Heating

3: 4.90 g / Dibal-H / toluene; CH₂Cl₂ / 0.5 h / -40 °C

4: NaH / dimethylformamide / 4 h / 0 °C

5: 50percent aq.HOAc / 22 h / Ambient temperature

6: pyridine, DMAP, NEt₃ / CH₂Cl₂ / 10 h / Ambient temperature

7: 78 percent / 60percent aq.CF₃COOH / 64 h / 5 °C

8: NaIO₄ / methanol; H₂O / 2 h / Ambient temperature

9: amberlite IR-120 (H+) / 7 h / 60 °C

10: pyridine / 6 h / 60 °C

11: 68 percent / N-methylmorpholine N-oxide (NMO) / OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 23 h / Ambient temperature

12: camphorsulfonic acid / acetone / 42 h / Ambient temperature

With pyridine; dmap; sodium periodate; Amberlite IR-120 (H+); sodium hydride; diisobutylaluminium hydride; ozone; acetic acid; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; trifluoroacetic acid; osmium(VIII) oxide; camphor-10-sulfonic acid; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4020(01)82015-9

Reference yield:

(3aR,5S,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-6-carbaldehyde (116612-14-7) → Benzoic acid (2R,3S,4R,5R)-4-((4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(2,2-dimethyl-propionyloxymethyl)-5-methoxy-4-methyl-tetrahydro-furan-3-yl ester (129662-87-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 90 percent / benzene / 12 h / Heating

2: 4.90 g / Dibal-H / toluene; CH₂Cl₂ / 0.5 h / -40 °C

3: NaH / dimethylformamide / 4 h / 0 °C

4: 50percent aq.HOAc / 22 h / Ambient temperature

5: pyridine, DMAP, NEt₃ / CH₂Cl₂ / 10 h / Ambient temperature

6: 78 percent / 60percent aq.CF₃COOH / 64 h / 5 °C

7: NaIO₄ / methanol; H₂O / 2 h / Ambient temperature

8: amberlite IR-120 (H+) / 7 h / 60 °C

9: pyridine / 6 h / 60 °C

10: 68 percent / N-methylmorpholine N-oxide (NMO) / OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 23 h / Ambient temperature

11: camphorsulfonic acid / acetone / 42 h / Ambient temperature

With pyridine; dmap; sodium periodate; Amberlite IR-120 (H+); sodium hydride; diisobutylaluminium hydride; acetic acid; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic acid; osmium(VIII) oxide; camphor-10-sulfonic acid; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4020(01)82015-9

Reference yield:

(E)-3-[(3aR,5S,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-prop-2-en-1-ol (116612-16-9) → Benzoic acid (2R,3S,4R,5R)-4-((4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(2,2-dimethyl-propionyloxymethyl)-5-methoxy-4-methyl-tetrahydro-furan-3-yl ester (129662-87-9)

Guidance literature:

Multi-step reaction with 9 steps

1: NaH / dimethylformamide / 4 h / 0 °C

2: 50percent aq.HOAc / 22 h / Ambient temperature

3: pyridine, DMAP, NEt₃ / CH₂Cl₂ / 10 h / Ambient temperature

4: 78 percent / 60percent aq.CF₃COOH / 64 h / 5 °C

5: NaIO₄ / methanol; H₂O / 2 h / Ambient temperature

6: amberlite IR-120 (H+) / 7 h / 60 °C

7: pyridine / 6 h / 60 °C

8: 68 percent / N-methylmorpholine N-oxide (NMO) / OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 23 h / Ambient temperature

9: camphorsulfonic acid / acetone / 42 h / Ambient temperature

With pyridine; dmap; sodium periodate; Amberlite IR-120 (H+); sodium hydride; acetic acid; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic acid; osmium(VIII) oxide; camphor-10-sulfonic acid; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;

DOI:10.1016/S0040-4020(01)82015-9

upstream raw materials:

(2R,3R,4S,5R)-4-(benzoyloxy)-3-<(1R,2R)-<3-(benzyloxy)-1,2-dihydroxy>propyl>-5-<<(2,2-dimethylpropionyl)oxy>methyl>-2-methoxy-3-methyltetrahydrofuran

2,2-dimethoxy-propane

3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-methyl-3-C-vinyl-α-D-allofuranose

(3aR,5S,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-6-carbaldehyde

Downstream raw materials:

(2R,3S,4S,5R)-3-<(1R,2R)-<3-(benzyloxy)-1,2-isopropylidenedioxy>propyl>-5-<<(2,2-dimethylpropionyl)oxy>methyl>-4-hydroxy-2-methoxy-3-methyltetrahydrofuran

[(2R,3S,4S)-3-Benzyloxy-4-((4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methoxy-4-methyl-tetrahydro-furan-2-yl]-methanol

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

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