(2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-(2-benzyloxy-1-benzyloxymethyl-ethoxy)-tetrahydro-pyran-2-carbaldehyde

Base Information

Chemical Name:(2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-(2-benzyloxy-1-benzyloxymethyl-ethoxy)-tetrahydro-pyran-2-carbaldehyde
CAS No.:444808-97-3
Molecular Formula:C₄₄H₄₆O₈
Molecular Weight:702.844
Hs Code.:

Synonyms:(2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-(2-benzyloxy-1-benzyloxymethyl-ethoxy)-tetrahydro-pyran-2-carbaldehyde

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Chemical Property of (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-(2-benzyloxy-1-benzyloxymethyl-ethoxy)-tetrahydro-pyran-2-carbaldehyde

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Technology Process of (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-(2-benzyloxy-1-benzyloxymethyl-ethoxy)-tetrahydro-pyran-2-carbaldehyde

There total 5 articles about (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-(2-benzyloxy-1-benzyloxymethyl-ethoxy)-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:

: 444808-94-0
1,3-di-O-benzyl-2-O-(2,3,4-tri-O-benzyl-β-D-galactopyranosyl)-glycerol

: 444808-97-3
(2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-(2-benzyloxy-1-benzyloxymethyl-ethoxy)-tetrahydro-pyran-2-carbaldehyde

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -60 - -40 ℃; for 1.5h;
DOI:10.1002/1099-0690(200204)2002:8<1429::AID-EJOC1429>3.0.CO;2-2

Reference yield:

: 6972-79-8
dibenzyl glycerol

: 444808-97-3
(2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-(2-benzyloxy-1-benzyloxymethyl-ethoxy)-tetrahydro-pyran-2-carbaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1.1: BF₃*OEt₂ / CH₂Cl₂ / 0 - 20 °C

1.2: 90 percent / NaOMe / methanol / 2 h

2.1: 80 percent / pyridine / 4 h / 55 °C

3.1: 94 percent / NaH / dimethylformamide / 0.5 h / 55 °C

4.1: 92 percent / HCl / H₂O; acetone / 0.75 h / Heating

5.1: 0.90 g / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -60 - -40 °C

With pyridine; hydrogenchloride; oxalyl dichloride; boron trifluoride diethyl etherate; sodium hydride; dimethyl sulfoxide; triethylamine; In dichloromethane; water; N,N-dimethyl-formamide; acetone; 1.2: Zemplen deacetylation / 5.1: Swern oxidation;
DOI:10.1002/1099-0690(200204)2002:8<1429::AID-EJOC1429>3.0.CO;2-2

Reference yield:

: 444808-91-7
1,3-di-O-benzyl-2-O-β-D-(galactopyranosyl)-glycerol

: 444808-97-3
(2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-(2-benzyloxy-1-benzyloxymethyl-ethoxy)-tetrahydro-pyran-2-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 80 percent / pyridine / 4 h / 55 °C

2: 94 percent / NaH / dimethylformamide / 0.5 h / 55 °C

3: 92 percent / HCl / H₂O; acetone / 0.75 h / Heating

4: 0.90 g / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -60 - -40 °C

With pyridine; hydrogenchloride; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In dichloromethane; water; N,N-dimethyl-formamide; acetone; 4: Swern oxidation;
DOI:10.1002/1099-0690(200204)2002:8<1429::AID-EJOC1429>3.0.CO;2-2