Acetic acid (4aS,6R,7R,8S,8aR)-8-benzyloxy-6-((3R,4R,5R,6R)-2,5-diacetoxy-3-azido-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Base Information

Chemical Name:Acetic acid (4aS,6R,7R,8S,8aR)-8-benzyloxy-6-((3R,4R,5R,6R)-2,5-diacetoxy-3-azido-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester
CAS No.:200274-29-9
Molecular Formula:C₃₅H₄₃N₃O₁₃
Molecular Weight:713.739
Hs Code.:

Acetic acid (4aS,6R,7R,8S,8aR)-8-benzyloxy-6-((3R,4R,5R,6R)-2,5-diacetoxy-3-azido-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Synonyms:Acetic acid (4aS,6R,7R,8S,8aR)-8-benzyloxy-6-((3R,4R,5R,6R)-2,5-diacetoxy-3-azido-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

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Chemical Property of Acetic acid (4aS,6R,7R,8S,8aR)-8-benzyloxy-6-((3R,4R,5R,6R)-2,5-diacetoxy-3-azido-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

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Technology Process of Acetic acid (4aS,6R,7R,8S,8aR)-8-benzyloxy-6-((3R,4R,5R,6R)-2,5-diacetoxy-3-azido-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

There total 1 articles about Acetic acid (4aS,6R,7R,8S,8aR)-8-benzyloxy-6-((3R,4R,5R,6R)-2,5-diacetoxy-3-azido-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-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: 90.0%

: 1,4-di-O-acetyl-2-azido-6-O-benzyl-2-deoxy-D-galactopyranose

: Acetic acid (4aS,6S,7R,8S,8aR)-8-benzyloxy-2,2-dimethyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

: 200274-29-9
Acetic acid (4aS,6R,7R,8S,8aR)-8-benzyloxy-6-((3R,4R,5R,6R)-2,5-diacetoxy-3-azido-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; for 0.25h;
DOI:10.1016/S0960-894X(97)10082-8

Reference yield: 77.0%

: 200274-29-9
Acetic acid (4aS,6R,7R,8S,8aR)-8-benzyloxy-6-((3R,4R,5R,6R)-2,5-diacetoxy-3-azido-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

: Acetic acid (4aS,6R,7R,8S,8aR)-6-((2R,3R,4R,5R)-3-acetoxy-5-azido-2-benzyloxymethyl-6-hydroxy-tetrahydro-pyran-4-yloxy)-8-benzyloxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Guidance literature:: With benzylamine; In diethyl ether; at 0 ℃; for 2h;
DOI:10.1016/S0960-894X(97)10082-8

Reference yield:

: 200274-29-9
Acetic acid (4aS,6R,7R,8S,8aR)-8-benzyloxy-6-((3R,4R,5R,6R)-2,5-diacetoxy-3-azido-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

: C₆₂H₇₄N₆O₂₄

Guidance literature:: Multi-step reaction with 8 steps

1: 77 percent / PhCH₂NH₂ / diethyl ether / 2 h / 0 °C

2: 70 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

3: 51 percent / TBDMSOTf / acetonitrile; CH₂Cl₂ / 0.17 h / -50 °C

4: 83 percent / TBAF / tetrahydrofuran / 2 h / 0 °C

5: (COCl)2, DIPEA / dimethylsulfoxide; CH₂Cl₂ / 1 h / -78 °C

6: NaClO₂, NaH₂PO₄, 2-methyl-2-butene / 2-methyl-propan-2-ol / 16 h / Ambient temperature

7: ethanol; methanol

8: 100 percent / aq. acetic acid / 2 h / 80 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; t-butyldimethylsiyl triflate; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; benzylamine; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; acetic acid; dimethyl sulfoxide; acetonitrile; tert-butyl alcohol;
DOI:10.1016/S0960-894X(97)10082-8