Acetic acid (2R,3R,4R,5S,6S)-4,5-diacetoxy-2-((3aR,6R,7R,7aR)-5-benzyl-7-benzyloxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-6-ylmethoxy)-6-methyl-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Acetic acid (2R,3R,4R,5S,6S)-4,5-diacetoxy-2-((3aR,6R,7R,7aR)-5-benzyl-7-benzyloxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-6-ylmethoxy)-6-methyl-tetrahydro-pyran-3-yl ester
CAS No.:634916-79-3
Molecular Formula:C₃₅H₄₅NO₁₁
Molecular Weight:655.742
Hs Code.:

Acetic acid (2R,3R,4R,5S,6S)-4,5-diacetoxy-2-((3aR,6R,7R,7aR)-5-benzyl-7-benzyloxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-6-ylmethoxy)-6-methyl-tetrahydro-pyran-3-yl ester

Synonyms:Acetic acid (2R,3R,4R,5S,6S)-4,5-diacetoxy-2-((3aR,6R,7R,7aR)-5-benzyl-7-benzyloxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-6-ylmethoxy)-6-methyl-tetrahydro-pyran-3-yl ester

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Chemical Property of Acetic acid (2R,3R,4R,5S,6S)-4,5-diacetoxy-2-((3aR,6R,7R,7aR)-5-benzyl-7-benzyloxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-6-ylmethoxy)-6-methyl-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2R,3R,4R,5S,6S)-4,5-diacetoxy-2-((3aR,6R,7R,7aR)-5-benzyl-7-benzyloxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-6-ylmethoxy)-6-methyl-tetrahydro-pyran-3-yl ester

There total 10 articles about Acetic acid (2R,3R,4R,5S,6S)-4,5-diacetoxy-2-((3aR,6R,7R,7aR)-5-benzyl-7-benzyloxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-6-ylmethoxy)-6-methyl-tetrahydro-pyran-3-yl 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: 87.0%

: 69980-52-5
2,3,4-tri-O-acetyl-L-rhamnopyranosyl bromide

: 121194-96-5
N-benzyl-4-O-benzyl-1,5-dideoxy-1,5-imino-2,3-O-isopropylidene-D-mannitol

: 634916-79-3
Acetic acid (2R,3R,4R,5S,6S)-4,5-diacetoxy-2-((3aR,6R,7R,7aR)-5-benzyl-7-benzyloxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-6-ylmethoxy)-6-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: With 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; toluene; at -10 ℃; for 0.5h;
DOI:10.1039/b304063a

Reference yield:

: 138913-30-1
(1R,4S,5S,6R)-3-chloro-4,5-O-isopropylidene-7-oxabicyclo[4.1.0]hept-2-ene-4,5-diol

: 634916-79-3
Acetic acid (2R,3R,4R,5S,6S)-4,5-diacetoxy-2-((3aR,6R,7R,7aR)-5-benzyl-7-benzyloxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-6-ylmethoxy)-6-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: 98 percent / LiCl; HOAc / tetrahydrofuran / 17 h / 18 °C

2.1: 91 percent / LiN₃ / dimethylformamide / 72 h / 18 °C

3.1: 100 percent / KI; NAH / tetrahydrofuran / 24 h / 0 - 18 °C

4.1: O₃; pyridine / 1 h / -78 °C

4.2: NaBH₄ / methanol / 3 h / -10 °C

5.1: imidazole / CH₂Cl₂ / 2 h / 18 °C

6.1: 86 percent / H₂ / 5percent Pd/C / ethyl acetate / 36 h / 18 °C / 760.05 Torr

7.1: BH₃*Me₂S / tetrahydrofuran / 4.5 h / 18 °C

7.2: 73 percent / MeOH / 10percent Pd/C / 38 h / 18 °C

8.1: KI; NaH / tetrahydrofuran / 24 h / 18 °C

9.1: TBAF / tetrahydrofuran / 2 h / 18 °C

10.1: 87 percent / AgOTf; 4 Angstroem molecular sieves / toluene; CH₂Cl₂ / 0.5 h / -10 °C

With pyridine; 1H-imidazole; lithium azide; dimethylsulfide borane complex; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; silver trifluoromethanesulfonate; sodium hydride; ozone; acetic acid; potassium iodide; lithium chloride; 5percent Pd/C; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1039/b304063a

Reference yield:

: 634916-74-8
(4S,5S)-5-[(1R,2R)-2-Azido-1-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester

: 634916-79-3
Acetic acid (2R,3R,4R,5S,6S)-4,5-diacetoxy-2-((3aR,6R,7R,7aR)-5-benzyl-7-benzyloxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-6-ylmethoxy)-6-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 86 percent / H₂ / 5percent Pd/C / ethyl acetate / 36 h / 18 °C / 760.05 Torr

2.1: BH₃*Me₂S / tetrahydrofuran / 4.5 h / 18 °C

2.2: 73 percent / MeOH / 10percent Pd/C / 38 h / 18 °C

3.1: KI; NaH / tetrahydrofuran / 24 h / 18 °C

4.1: TBAF / tetrahydrofuran / 2 h / 18 °C

5.1: 87 percent / AgOTf; 4 Angstroem molecular sieves / toluene; CH₂Cl₂ / 0.5 h / -10 °C

With dimethylsulfide borane complex; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; silver trifluoromethanesulfonate; sodium hydride; potassium iodide; 5percent Pd/C; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;
DOI:10.1039/b304063a