3,4-di-O-benzyl-6,7-didehydro-6,7-dideoxy-7-C-isopropyl-2-O-methyl-β-D-gulono-1,5-lactone

Base Information

• Chemical Name: 3,4-di-O-benzyl-6,7-didehydro-6,7-dideoxy-7-C-isopropyl-2-O-methyl-β-D-gulono-1,5-lactone
• CAS No.: 142929-71-3
• Molecular Formula: C₂₅H₃₀O₅
• Molecular Weight: 410.51

Synonyms:3,4-di-O-benzyl-6,7-didehydro-6,7-dideoxy-7-C-isopropyl-2-O-methyl-β-D-gulono-1,5-lactone

Chemical Property of 3,4-di-O-benzyl-6,7-didehydro-6,7-dideoxy-7-C-isopropyl-2-O-methyl-β-D-gulono-1,5-lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4-di-O-benzyl-6,7-didehydro-6,7-dideoxy-7-C-isopropyl-2-O-methyl-β-D-gulono-1,5-lactone

There total 11 articles about 3,4-di-O-benzyl-6,7-didehydro-6,7-dideoxy-7-C-isopropyl-2-O-methyl-β-D-gulono-1,5-lactone 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-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-gulofuranose (26775-14-4) → 3,4-di-O-benzyl-6,7-didehydro-6,7-dideoxy-7-C-isopropyl-2-O-methyl-β-D-gulono-1,5-lactone (142929-71-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 83 percent / KOH / 2 h / 140 °C

2: 65 percent / Dowex 50W / 20 h / Heating

3: 87 percent / p-TsOH / CH₂Cl₂ / 1 h / Ambient temperature

4: 89 percent / NaH / dimethylformamide; paraffin / 5 h / Ambient temperature

5: 75 percent / DIBALH / CH₂Cl₂; toluene / 10 h / Ambient temperature

6: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -70 deg C, 30 min, 2) CH₂Cl₂, -70 deg C to r.t.

7: n-BuLi / tetrahydrofuran / 0.5 h / 0 °C

8: pyridine, DMAP / 12 h / Ambient temperature

9: 88 percent / Na₂HPO₄, 5percent Na(Hg) / 4 h / 0 °C

10: 50percent AcOH / 20 h / 110 °C

11: DMSO, Ac₂O / 24 h / Ambient temperature

With pyridine; dmap; potassium hydroxide; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; oxalyl dichloride; Dowex 50W; acetic anhydride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; paraffin;

DOI:10.1021/jo00044a053

Reference yield:

3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-gulofuranoside (23885-38-3) → 3,4-di-O-benzyl-6,7-didehydro-6,7-dideoxy-7-C-isopropyl-2-O-methyl-β-D-gulono-1,5-lactone (142929-71-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 65 percent / Dowex 50W / 20 h / Heating

2: 87 percent / p-TsOH / CH₂Cl₂ / 1 h / Ambient temperature

3: 89 percent / NaH / dimethylformamide; paraffin / 5 h / Ambient temperature

4: 75 percent / DIBALH / CH₂Cl₂; toluene / 10 h / Ambient temperature

5: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -70 deg C, 30 min, 2) CH₂Cl₂, -70 deg C to r.t.

6: n-BuLi / tetrahydrofuran / 0.5 h / 0 °C

7: pyridine, DMAP / 12 h / Ambient temperature

8: 88 percent / Na₂HPO₄, 5percent Na(Hg) / 4 h / 0 °C

9: 50percent AcOH / 20 h / 110 °C

10: DMSO, Ac₂O / 24 h / Ambient temperature

With pyridine; dmap; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; oxalyl dichloride; Dowex 50W; acetic anhydride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; paraffin;

DOI:10.1021/jo00044a053

Reference yield:

methyl 3,4-di-O-benzyl-2-O-methyl-β-D-gulopyranoside (142929-67-7) → 3,4-di-O-benzyl-6,7-didehydro-6,7-dideoxy-7-C-isopropyl-2-O-methyl-β-D-gulono-1,5-lactone (142929-71-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -70 deg C, 30 min, 2) CH₂Cl₂, -70 deg C to r.t.

2: n-BuLi / tetrahydrofuran / 0.5 h / 0 °C

3: pyridine, DMAP / 12 h / Ambient temperature

4: 88 percent / Na₂HPO₄, 5percent Na(Hg) / 4 h / 0 °C

5: 50percent AcOH / 20 h / 110 °C

6: DMSO, Ac₂O / 24 h / Ambient temperature

With pyridine; dmap; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; oxalyl dichloride; acetic anhydride; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran;

DOI:10.1021/jo00044a053

upstream raw materials:

3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-gulofuranose

3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-gulofuranoside

methyl 3,4-di-O-benzyl-2-O-methyl-β-D-gulopyranoside

(2S,3R,4R,5R,6R)-3,4-Bis-benzyloxy-5,6-dimethoxy-tetrahydro-pyran-2-carbaldehyde

Downstream raw materials:

cis-6,7-di-O-benzylbengamide E

6,7-di-O-benzylbengamide E

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