(3aR,5R,6S,6aR)-6-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Base Information

Chemical Name:(3aR,5R,6S,6aR)-6-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole
CAS No.:79384-20-6
Molecular Formula:C₃₉H₄₈O₁₀
Molecular Weight:676.804
Hs Code.:

(3aR,5R,6S,6aR)-6-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

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Chemical Property of (3aR,5R,6S,6aR)-6-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

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Technology Process of (3aR,5R,6S,6aR)-6-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

There total 4 articles about (3aR,5R,6S,6aR)-6-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole 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: 78.0%

: 350255-13-9
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

: 128573-17-1
(2R,3S,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-tetrahydro-pyran

: 79384-20-6,79384-23-9
(3aR,5R,6aR)-6-((2R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane;
DOI:10.1039/c39900000270

Reference yield:

: 55628-54-1
3,4,6-tri-O-benzyl-D-glucal

: 79384-20-6,79384-23-9
(3aR,5R,6S,6aR)-6-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 3 steps

1: toluene / 1 h / 25 °C

2: molecular sieves 4A / TMSOTf / diethyl ether / 0.25 h / 0 °C

3: Ph₃SnH / toluene / Heating

With 4 A molecular sieve; triphenylstannane; trimethylsilyl trifluoromethanesulfonate; In diethyl ether; toluene;
DOI:10.1016/S0040-4039(01)80327-0

Reference yield:

: 120316-50-9
Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-phenylselanyl-tetrahydro-pyran-2-yl ester

: 79384-20-6,79384-23-9
(3aR,5R,6S,6aR)-6-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 2 steps

1: molecular sieves 4A / TMSOTf / diethyl ether / 0.25 h / 0 °C

2: Ph₃SnH / toluene / Heating

With 4 A molecular sieve; triphenylstannane; trimethylsilyl trifluoromethanesulfonate; In diethyl ether; toluene;
DOI:10.1016/S0040-4039(01)80327-0