(1R,4R,6R,8R,9S,10S)-9,10-bis(benzyloxy)-8-benzyloxymethyl-2,7-dioxabicyclo[4.4.0.]decane-4-yl methanesulfonate

Base Information

Chemical Name:(1R,4R,6R,8R,9S,10S)-9,10-bis(benzyloxy)-8-benzyloxymethyl-2,7-dioxabicyclo[4.4.0.]decane-4-yl methanesulfonate
CAS No.:695188-85-3
Molecular Formula:C₃₁H₃₆O₈S
Molecular Weight:568.688
Hs Code.:

Synonyms:(1R,4R,6R,8R,9S,10S)-9,10-bis(benzyloxy)-8-benzyloxymethyl-2,7-dioxabicyclo[4.4.0.]decane-4-yl methanesulfonate

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Chemical Property of (1R,4R,6R,8R,9S,10S)-9,10-bis(benzyloxy)-8-benzyloxymethyl-2,7-dioxabicyclo[4.4.0.]decane-4-yl methanesulfonate

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Technology Process of (1R,4R,6R,8R,9S,10S)-9,10-bis(benzyloxy)-8-benzyloxymethyl-2,7-dioxabicyclo[4.4.0.]decane-4-yl methanesulfonate

There total 6 articles about (1R,4R,6R,8R,9S,10S)-9,10-bis(benzyloxy)-8-benzyloxymethyl-2,7-dioxabicyclo[4.4.0.]decane-4-yl methanesulfonate 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: 56.0%

: 124-63-0
methanesulfonyl chloride

: 695188-83-1
(4aR,6R,7R,8R,8aS)-7,8-Bis-benzyloxy-6-benzyloxymethyl-octahydro-pyrano[3,2-b]pyran-3-ol

: 695188-84-2
(1R,4S,6R,8R,9S,10S)-9,10-bis(benzyloxy)-8-benzyloxymethyl-2,7-dioxabicyclo[4.4.0]decane-4-yl methanesulfonate

: 695188-85-3
(1R,4R,6R,8R,9S,10S)-9,10-bis(benzyloxy)-8-benzyloxymethyl-2,7-dioxabicyclo[4.4.0.]decane-4-yl methanesulfonate

Guidance literature:: With triethylamine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1055/s-2004-820021

Reference yield:

: 135637-05-7
2-(3',4',6'-tri-O-benzyl-α-D-glucopyranosyl)-(Z)-styrene

: 695188-85-3
(1R,4R,6R,8R,9S,10S)-9,10-bis(benzyloxy)-8-benzyloxymethyl-2,7-dioxabicyclo[4.4.0.]decane-4-yl methanesulfonate

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / tetrabutylammonium iodide; sodium hydride / dimethylformamide / 16 h

2: 82 percent / tetrahydrofuran / 48 h / Heating

3: 88 percent / Cl₂(tricyclophosphane)-ruthenium complex / CH₂Cl₂ / Heating

4: 92 percent / TFA / CH₂Cl₂; H₂O / 0.5 h

5: L-selectride / tetrahydrofuran / 16 h / 20 °C

6: 191 mg / triethylamine / CH₂Cl₂ / 4 h

With Cl₂(tricyclophosphane)-ruthenium; tetra-(n-butyl)ammonium iodide; L-Selectride; sodium hydride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 2: Petasis olefination;
DOI:10.1002/ejoc.200600228

Reference yield:

: 695188-78-4
[(2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((Z)-styryl)-tetrahydro-pyran-3-yloxy]-acetic acid methyl ester

: 695188-85-3
(1R,4R,6R,8R,9S,10S)-9,10-bis(benzyloxy)-8-benzyloxymethyl-2,7-dioxabicyclo[4.4.0.]decane-4-yl methanesulfonate

Guidance literature:: Multi-step reaction with 5 steps

1: 82 percent / tetrahydrofuran / 48 h / Heating

2: 88 percent / Cl₂(tricyclophosphane)-ruthenium complex / CH₂Cl₂ / Heating

3: 92 percent / TFA / CH₂Cl₂; H₂O / 0.5 h

4: L-selectride / tetrahydrofuran / 16 h / 20 °C

5: 191 mg / triethylamine / CH₂Cl₂ / 4 h

With Cl₂(tricyclophosphane)-ruthenium; L-Selectride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; 1: Petasis olefination;
DOI:10.1002/ejoc.200600228