methyl 3,4-di-O-benzyl-6,7-didehydro-6,7-dideoxy-7-C-isopropyl-2-O-methyl-β-D-guloheptopyranoside

Base Information

Chemical Name:methyl 3,4-di-O-benzyl-6,7-didehydro-6,7-dideoxy-7-C-isopropyl-2-O-methyl-β-D-guloheptopyranoside
CAS No.:142929-70-2
Molecular Formula:C₂₆H₃₄O₅
Molecular Weight:426.553
Hs Code.:

Synonyms:methyl 3,4-di-O-benzyl-6,7-didehydro-6,7-dideoxy-7-C-isopropyl-2-O-methyl-β-D-guloheptopyranoside

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

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

There total 9 articles about methyl 3,4-di-O-benzyl-6,7-didehydro-6,7-dideoxy-7-C-isopropyl-2-O-methyl-β-D-guloheptopyranoside 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: 88.0%

: 142929-68-8
Acetic acid 2-benzenesulfonyl-1-((2S,3R,4R,5R,6R)-3,4-bis-benzyloxy-5,6-dimethoxy-tetrahydro-pyran-2-yl)-3-methyl-butyl ester

: 142929-70-2
methyl 3,4-di-O-benzyl-6,7-didehydro-6,7-dideoxy-7-C-isopropyl-2-O-methyl-β-D-guloheptopyranoside

Guidance literature:: With disodium hydrogenphosphate; sodium amalgam; at 0 ℃; for 4h;
DOI:10.1021/jo00044a053

Reference yield:

: 26775-14-4
3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-gulofuranose

: 142929-70-2
methyl 3,4-di-O-benzyl-6,7-didehydro-6,7-dideoxy-7-C-isopropyl-2-O-methyl-β-D-guloheptopyranoside

Guidance literature:: Multi-step reaction with 9 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

With pyridine; dmap; potassium hydroxide; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; oxalyl dichloride; Dowex 50W; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; paraffin;
DOI:10.1021/jo00044a053

Reference yield:

: 23885-38-3
3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-gulofuranoside

: 142929-70-2
methyl 3,4-di-O-benzyl-6,7-didehydro-6,7-dideoxy-7-C-isopropyl-2-O-methyl-β-D-guloheptopyranoside

Guidance literature:: Multi-step reaction with 8 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

With pyridine; dmap; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; oxalyl dichloride; Dowex 50W; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; paraffin;
DOI:10.1021/jo00044a053