(3aR,5R,5aS,8aS,8bR)-5-((((2S,3R,4R,5R)-3,4-Bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)methyl)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran

Base Information

Chemical Name:(3aR,5R,5aS,8aS,8bR)-5-((((2S,3R,4R,5R)-3,4-Bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)methyl)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran
CAS No.:88999-59-1
Molecular Formula:C₃₈H₄₆O₁₀
Molecular Weight:662.777
Hs Code.:

(3aR,5R,5aS,8aS,8bR)-5-((((2S,3R,4R,5R)-3,4-Bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)methyl)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran

Synonyms:(3aR,5R,5aS,8aS,8bR)-5-((((2S,3R,4R,5R)-3,4-Bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)methyl)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran

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Chemical Property of (3aR,5R,5aS,8aS,8bR)-5-((((2S,3R,4R,5R)-3,4-Bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)methyl)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran

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Technology Process of (3aR,5R,5aS,8aS,8bR)-5-((((2S,3R,4R,5R)-3,4-Bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)methyl)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran

There total 11 articles about (3aR,5R,5aS,8aS,8bR)-5-((((2S,3R,4R,5R)-3,4-Bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)methyl)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran 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: 91.0%

: C₂₆H₂₇IO₄

: 4064-06-6
1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

: 88999-59-1
(3aR,5R,5aS,8aS,8bR)-5-((((2S,3R,4R,5R)-3,4-Bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)methyl)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran

Guidance literature:: With N-ethyl-N,N-diisopropylamine; Triphenylphosphine oxide; In dichloromethane; at 0 ℃; for 2h; Molecular sieve;
DOI:10.1021/jo500632h

Reference yield: 81.0%

: 96689-78-0
2-pyridyl 2,3,5-tri-O-benzyl-1-thio-β-D-ribofuranoside

: 4064-06-6
1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

: 88999-59-1
(3aR,5R,5aS,8aS,8bR)-5-((((2S,3R,4R,5R)-3,4-Bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)methyl)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran

Guidance literature:: With methyl iodide; In dichloromethane;
DOI:10.1016/S0040-4020(01)89016-5

Reference yield:

: 2,3,5-tri-O-benzyl-α-D-ribofuranose

: 88999-59-1
(3aR,5R,5aS,8aS,8bR)-5-((((2S,3R,4R,5R)-3,4-Bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)methyl)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran

: 1,2:3,4-di-O-isopropylidene-6-O-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)-α-D-galactopyranose

Guidance literature:: Multi-step reaction with 2 steps

1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere

2: (R)-4-(3-(3,5-Bis(trifluoromethyl)phenyl)thioureido)-3,3-dimethyl-5-oxo-5-(pyrrolidin-1-yl)pentyl 3-(3-((R)-3,3-dimethyl-1-((S)-2-methyl-2-(naphthalen-2-yl)pyrrolidin-1-yl)-1-oxobutan-2-yl)thioureido)-5-(trifluoromethyl)benzoate / 18 h / 40 °C / Molecular sieve; Inert atmosphere

With dmap; (R)-4-(3-(3,5-Bis(trifluoromethyl)phenyl)thioureido)-3,3-dimethyl-5-oxo-5-(pyrrolidin-1-yl)pentyl 3-(3-((R)-3,3-dimethyl-1-((S)-2-methyl-2-(naphthalen-2-yl)pyrrolidin-1-yl)-1-oxobutan-2-yl)thioureido)-5-(trifluoromethyl)benzoate; In dichloromethane;
DOI:10.1021/jacs.0c00335