Acetic acid (1R,2R)-2,3-diacetoxy-1-[(3aS,4S,6R,7aS)-6-formyl-2-oxo-6-((2R,3R,4S,5R,6R)-2,3,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-ylmethyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-propyl ester

Base Information

Chemical Name:Acetic acid (1R,2R)-2,3-diacetoxy-1-[(3aS,4S,6R,7aS)-6-formyl-2-oxo-6-((2R,3R,4S,5R,6R)-2,3,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-ylmethyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-propyl ester
CAS No.:1054827-43-8
Molecular Formula:C₅₁H₅₆O₁₆
Molecular Weight:924.996
Hs Code.:

Acetic acid (1R,2R)-2,3-diacetoxy-1-[(3aS,4S,6R,7aS)-6-formyl-2-oxo-6-((2R,3R,4S,5R,6R)-2,3,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-ylmethyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-propyl ester

Synonyms:Acetic acid (1R,2R)-2,3-diacetoxy-1-[(3aS,4S,6R,7aS)-6-formyl-2-oxo-6-((2R,3R,4S,5R,6R)-2,3,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-ylmethyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-propyl ester

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Chemical Property of Acetic acid (1R,2R)-2,3-diacetoxy-1-[(3aS,4S,6R,7aS)-6-formyl-2-oxo-6-((2R,3R,4S,5R,6R)-2,3,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-ylmethyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-propyl ester

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Technology Process of Acetic acid (1R,2R)-2,3-diacetoxy-1-[(3aS,4S,6R,7aS)-6-formyl-2-oxo-6-((2R,3R,4S,5R,6R)-2,3,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-ylmethyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-propyl ester

There total 9 articles about Acetic acid (1R,2R)-2,3-diacetoxy-1-[(3aS,4S,6R,7aS)-6-formyl-2-oxo-6-((2R,3R,4S,5R,6R)-2,3,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-ylmethyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-propyl ester 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:

: 352211-97-3
benzyl 2,4,6-tri-O-benzyl-3-deoxy-3-C-[(7,8,9-tri-O-acetyl-2,6-anhydro-4,5-O-carbonylidene-1,3-dideoxy-1-phenylselenyl-D-erythro-L-talo-nonit-2-yl)-methyl]-β-D-galacto-hexopyranoside

: 1054827-43-8
Acetic acid (1R,2R)-2,3-diacetoxy-1-[(3aS,4S,6R,7aS)-6-formyl-2-oxo-6-((2R,3R,4S,5R,6R)-2,3,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-ylmethyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-propyl ester

Guidance literature:: benzyl 2,4,6-tri-O-benzyl-3-deoxy-3-C-[(7,8,9-tri-O-acetyl-2,6-anhydro-4,5-O-carbonylidene-1,3-dideoxy-1-phenylselenyl-D-erythro-L-talo-nonit-2-yl)-methyl]-β-D-galacto-hexopyranoside; With 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; at -80 ℃; for 0.25h;

With sodium acetate; acetic anhydride; In tetrahydrofuran; for 1.5h; Further stages.; Heating;
DOI:10.1021/jo015543l

Reference yield:

: (4S,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-5-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-1-((2R,3R,4S,5R,6R)-2,3,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yl)-pentan-2-ol

: 1054827-43-8
Acetic acid (1R,2R)-2,3-diacetoxy-1-[(3aS,4S,6R,7aS)-6-formyl-2-oxo-6-((2R,3R,4S,5R,6R)-2,3,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-ylmethyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-propyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 95 percent / Dess-Martin-periodinane / CH₂Cl₂

2.1: 62 percent / toluene; tetrahydrofuran / -40 - 20 °C

3.1: 94 percent / TBAF / tetrahydrofuran / 40 °C

4.1: 95 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

5.1: 69 percent / aq. TFA / tetrahydrofuran / 0.83 h / Heating

6.1: various solvent(s) / 1 h / -80 °C

7.1: 317 mg / pyridine / CH₂Cl₂ / 20 °C

8.1: mCPBA / tetrahydrofuran / 0.25 h / -80 °C

8.2: Ac₂O; NaOAc / tetrahydrofuran / 1.5 h / Heating

With pyridine; tetrabutyl ammonium fluoride; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jo015543l

Reference yield:

: 352211-86-0
benzyl 2,4,6-tri-O-benzyl-3-deoxy-3-C-[1,2,3-trideoxy-6,7:8,9-di-O-isopropylidene-2-methylene-D-glycero-D-gulo-non-2-ulos-1-yl]-β-D-galacto-hexopyranoside

: 1054827-43-8
Acetic acid (1R,2R)-2,3-diacetoxy-1-[(3aS,4S,6R,7aS)-6-formyl-2-oxo-6-((2R,3R,4S,5R,6R)-2,3,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-ylmethyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-propyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 95 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

2.1: 69 percent / aq. TFA / tetrahydrofuran / 0.83 h / Heating

3.1: various solvent(s) / 1 h / -80 °C

4.1: 317 mg / pyridine / CH₂Cl₂ / 20 °C

5.1: mCPBA / tetrahydrofuran / 0.25 h / -80 °C

5.2: Ac₂O; NaOAc / tetrahydrofuran / 1.5 h / Heating

With pyridine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo015543l