4,8:11,15-dianhydro-5,6,7,12,13,14,16-hepta-O-benzyl-1,2,3,9,10-pentadeoxy-D-erythro-L-talo-D-ido-hexadec-1-enitol

Base Information

Chemical Name:4,8:11,15-dianhydro-5,6,7,12,13,14,16-hepta-O-benzyl-1,2,3,9,10-pentadeoxy-D-erythro-L-talo-D-ido-hexadec-1-enitol
CAS No.:405071-89-8
Molecular Formula:C₆₅H₇₀O₉
Molecular Weight:995.265
Hs Code.:

Synonyms:4,8:11,15-dianhydro-5,6,7,12,13,14,16-hepta-O-benzyl-1,2,3,9,10-pentadeoxy-D-erythro-L-talo-D-ido-hexadec-1-enitol

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Chemical Property of 4,8:11,15-dianhydro-5,6,7,12,13,14,16-hepta-O-benzyl-1,2,3,9,10-pentadeoxy-D-erythro-L-talo-D-ido-hexadec-1-enitol

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Technology Process of 4,8:11,15-dianhydro-5,6,7,12,13,14,16-hepta-O-benzyl-1,2,3,9,10-pentadeoxy-D-erythro-L-talo-D-ido-hexadec-1-enitol

There total 4 articles about 4,8:11,15-dianhydro-5,6,7,12,13,14,16-hepta-O-benzyl-1,2,3,9,10-pentadeoxy-D-erythro-L-talo-D-ido-hexadec-1-enitol 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: 80.0%

: 405071-88-7
1-O-acetyl 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-α,β-D-glycero-D-gulo-D-gluco-tridecopyranose

: 762-72-1
allyl-trimethyl-silane

: 405071-89-8
4,8:11,15-dianhydro-5,6,7,12,13,14,16-hepta-O-benzyl-1,2,3,9,10-pentadeoxy-D-erythro-L-talo-D-ido-hexadec-1-enitol

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1039/b106029p

Reference yield:

: 139242-12-9
methyl 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-α-D-glycero-D-gulo-D-gluco-tridecopyranoside

: 405071-89-8
4,8:11,15-dianhydro-5,6,7,12,13,14,16-hepta-O-benzyl-1,2,3,9,10-pentadeoxy-D-erythro-L-talo-D-ido-hexadec-1-enitol

Guidance literature:: Multi-step reaction with 3 steps

1: aq. AcOH; H₂SO₄ / 1.25 h / 100 °C

2: 425 mg / pyridine / 3 h / 20 °C

3: 80 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sulfuric acid; acetic acid; In dichloromethane;
DOI:10.1039/b106029p

Reference yield:

: 252851-44-8
methyl 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-α-D-glycero-D-gulo-tridec-6-enopyranoside

: 405071-89-8
4,8:11,15-dianhydro-5,6,7,12,13,14,16-hepta-O-benzyl-1,2,3,9,10-pentadeoxy-D-erythro-L-talo-D-ido-hexadec-1-enitol

Guidance literature:: Multi-step reaction with 4 steps

1: 91 percent / TsNHNH₂; aq. AcONa / 1,2-dimethoxy-ethane / 1 h / 85 °C

2: aq. AcOH; H₂SO₄ / 1.25 h / 100 °C

3: 425 mg / pyridine / 3 h / 20 °C

4: 80 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sulfuric acid; sodium acetate; acetic acid; toluene-4-sulfonic acid hydrazide; In 1,2-dimethoxyethane; dichloromethane;
DOI:10.1039/b106029p