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

Base Information

• Chemical Name: (2S,3S,4S)-3-Benzyloxy-4-((4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methoxy-4-methyl-tetrahydro-furan-2-carbaldehyde
• CAS No.: 129662-89-1
• Molecular Formula: C₂₇H₃₄O₇
• Molecular Weight: 470.563
• Mol file: 129662-89-1.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 18 articles about (2S,3S,4S)-3-Benzyloxy-4-((4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methoxy-4-methyl-tetrahydro-furan-2-carbaldehyde 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) → (2S,3S,4S,5R)-3-Benzyloxy-4-((4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methoxy-4-methyl-tetrahydro-furan-2-carbaldehyde (129662-89-1)

Guidance literature:

Multi-step reaction with 16 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

13: 1M NaOMe / methanol / 1.5 h / 0 °C

14: NaH / dimethylformamide / 15 h / Ambient temperature

15: 1M NaOMe / methanol / 20 h / Ambient temperature

16: oxalyl chloride, DMSO / CH₂Cl₂ / 1a) -78 deg C, 90 min 1b) Et₃N, up to r.t., 1 h

With pyridine; dmap; sodium periodate; oxalyl dichloride; Amberlite IR-120 (H+); sodium methylate; sodium hydride; diisobutylaluminium hydride; ozone; acetic acid; dimethyl sulfoxide; 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) → (2S,3S,4S,5R)-3-Benzyloxy-4-((4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methoxy-4-methyl-tetrahydro-furan-2-carbaldehyde (129662-89-1)

Guidance literature:

Multi-step reaction with 15 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

12: 1M NaOMe / methanol / 1.5 h / 0 °C

13: NaH / dimethylformamide / 15 h / Ambient temperature

14: 1M NaOMe / methanol / 20 h / Ambient temperature

15: oxalyl chloride, DMSO / CH₂Cl₂ / 1a) -78 deg C, 90 min 1b) Et₃N, up to r.t., 1 h

With pyridine; dmap; sodium periodate; oxalyl dichloride; Amberlite IR-120 (H+); sodium methylate; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; 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) → (2S,3S,4S,5R)-3-Benzyloxy-4-((4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methoxy-4-methyl-tetrahydro-furan-2-carbaldehyde (129662-89-1)

Guidance literature:

Multi-step reaction with 13 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

10: 1M NaOMe / methanol / 1.5 h / 0 °C

11: NaH / dimethylformamide / 15 h / Ambient temperature

12: 1M NaOMe / methanol / 20 h / Ambient temperature

13: oxalyl chloride, DMSO / CH₂Cl₂ / 1a) -78 deg C, 90 min 1b) Et₃N, up to r.t., 1 h

With pyridine; dmap; sodium periodate; oxalyl dichloride; Amberlite IR-120 (H+); sodium methylate; sodium hydride; acetic acid; dimethyl sulfoxide; 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,3S,4S,5R)-4-(benzyloxy)-3-<(1R,2R)-<3-(benzyloxy)-1,2-(isopropylidenedioxy)>propyl>-5-(hydroxymethyl)-2-methoxy-3-methyltetrahydrofuran

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

(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

Downstream raw materials:

asteltoxin

(2R,3S,4S,5R)-4-(benzyloxy)-3-<(1R,2R)-<3-(benzyloxy)-1,2-(isopropylidenedioxy)>propyl>-2-methoxy-3-methyl-5-vinyltetrahydrofuran