1,3-di-O-benzyl-2-O-[(6Z)-2,3,4-tri-O-benzyl-6,7,8,9,10,11,12,13-octadeoxy-β-D-galacto-tridec-6-enopyranosyl]glycerol

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Chemical Name:1,3-di-O-benzyl-2-O-[(6Z)-2,3,4-tri-O-benzyl-6,7,8,9,10,11,12,13-octadeoxy-β-D-galacto-tridec-6-enopyranosyl]glycerol
CAS No.:444808-98-4
Molecular Formula:C₅₁H₆₀O₇
Molecular Weight:785.033
Hs Code.:

Synonyms:1,3-di-O-benzyl-2-O-[(6Z)-2,3,4-tri-O-benzyl-6,7,8,9,10,11,12,13-octadeoxy-β-D-galacto-tridec-6-enopyranosyl]glycerol

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Chemical Property of 1,3-di-O-benzyl-2-O-[(6Z)-2,3,4-tri-O-benzyl-6,7,8,9,10,11,12,13-octadeoxy-β-D-galacto-tridec-6-enopyranosyl]glycerol

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Technology Process of 1,3-di-O-benzyl-2-O-[(6Z)-2,3,4-tri-O-benzyl-6,7,8,9,10,11,12,13-octadeoxy-β-D-galacto-tridec-6-enopyranosyl]glycerol

There total 6 articles about 1,3-di-O-benzyl-2-O-[(6Z)-2,3,4-tri-O-benzyl-6,7,8,9,10,11,12,13-octadeoxy-β-D-galacto-tridec-6-enopyranosyl]glycerol 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: 46.0%

: 13423-48-8
triphenylheptylphosphonium bromide

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

: 444808-98-4
1,3-di-O-benzyl-2-O-[(6Z)-2,3,4-tri-O-benzyl-6,7,8,9,10,11,12,13-octadeoxy-β-D-galacto-tridec-6-enopyranosyl]glycerol

Guidance literature:: With n-butyllithium; In tetrahydrofuran; hexane; at -50 ℃; for 0.666667h;
DOI:10.1002/1099-0690(200204)2002:8<1429::AID-EJOC1429>3.0.CO;2-2

Reference yield:

: 6972-79-8
dibenzyl glycerol

: 444808-98-4
1,3-di-O-benzyl-2-O-[(6Z)-2,3,4-tri-O-benzyl-6,7,8,9,10,11,12,13-octadeoxy-β-D-galacto-tridec-6-enopyranosyl]glycerol

Guidance literature:: Multi-step reaction with 6 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

6.1: 46 percent / BuLi / hexane; tetrahydrofuran / 0.67 h / -50 °C

With pyridine; hydrogenchloride; n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; 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

: 444808-98-4
1,3-di-O-benzyl-2-O-[(6Z)-2,3,4-tri-O-benzyl-6,7,8,9,10,11,12,13-octadeoxy-β-D-galacto-tridec-6-enopyranosyl]glycerol

Guidance literature:: Multi-step reaction with 5 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

5: 46 percent / BuLi / hexane; tetrahydrofuran / 0.67 h / -50 °C

With pyridine; hydrogenchloride; n-butyllithium; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; 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