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

Base Information

Chemical Name:(2S,3R,4R,5R,6R)-3,4-Bis-benzyloxy-5,6-dimethoxy-tetrahydro-pyran-2-carbaldehyde
CAS No.:1053613-62-9
Molecular Formula:C₂₂H₂₆O₆
Molecular Weight:386.445
Hs Code.:

Synonyms:

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

Chemical Property:

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

There total 6 articles about (2S,3R,4R,5R,6R)-3,4-Bis-benzyloxy-5,6-dimethoxy-tetrahydro-pyran-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:

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

: 1053613-62-9
(2S,3R,4R,5R,6R)-3,4-Bis-benzyloxy-5,6-dimethoxy-tetrahydro-pyran-2-carbaldehyde

Guidance literature:: Multi-step reaction with 6 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.

With potassium hydroxide; oxalyl dichloride; Dowex 50W; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In 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

: 1053613-62-9
(2S,3R,4R,5R,6R)-3,4-Bis-benzyloxy-5,6-dimethoxy-tetrahydro-pyran-2-carbaldehyde

Guidance literature:: Multi-step reaction with 5 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.

With oxalyl dichloride; Dowex 50W; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In dichloromethane; N,N-dimethyl-formamide; toluene; paraffin;
DOI:10.1021/jo00044a053

Reference yield:

: 143058-64-4
methyl 3-O-benzyl-4,6-O-benzylidene-2-O-methyl-β-D-gulopyranoside

: 1053613-62-9
(2S,3R,4R,5R,6R)-3,4-Bis-benzyloxy-5,6-dimethoxy-tetrahydro-pyran-2-carbaldehyde

Guidance literature:: Multi-step reaction with 2 steps

1: 75 percent / DIBALH / CH₂Cl₂; toluene / 10 h / Ambient temperature

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

With oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In dichloromethane; toluene;
DOI:10.1021/jo00044a053