(2S,3aR,4R,5S,6R,7aR)-2-allyl-4,5-bis(benzyloxy)-6-[(methanesulfonyloxy)methyl]2-methylhexahydro-furo[2,3-b]pyran

Base Information

Chemical Name:(2S,3aR,4R,5S,6R,7aR)-2-allyl-4,5-bis(benzyloxy)-6-[(methanesulfonyloxy)methyl]2-methylhexahydro-furo[2,3-b]pyran
CAS No.:1448160-28-8
Molecular Formula:C₂₇H₃₄O₇S
Molecular Weight:502.629
Hs Code.:

Synonyms:(2S,3aR,4R,5S,6R,7aR)-2-allyl-4,5-bis(benzyloxy)-6-[(methanesulfonyloxy)methyl]2-methylhexahydro-furo[2,3-b]pyran

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Chemical Property of (2S,3aR,4R,5S,6R,7aR)-2-allyl-4,5-bis(benzyloxy)-6-[(methanesulfonyloxy)methyl]2-methylhexahydro-furo[2,3-b]pyran

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Technology Process of (2S,3aR,4R,5S,6R,7aR)-2-allyl-4,5-bis(benzyloxy)-6-[(methanesulfonyloxy)methyl]2-methylhexahydro-furo[2,3-b]pyran

There total 3 articles about (2S,3aR,4R,5S,6R,7aR)-2-allyl-4,5-bis(benzyloxy)-6-[(methanesulfonyloxy)methyl]2-methylhexahydro-furo[2,3-b]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: 90.0%

: 1448160-12-0
C₂₄H₂₈O₇S

: 762-72-1
allyl-trimethyl-silane

: 1448160-28-8
(2S,3aR,4R,5S,6R,7aR)-2-allyl-4,5-bis(benzyloxy)-6-[(methanesulfonyloxy)methyl]2-methylhexahydro-furo[2,3-b]pyran

Guidance literature:: With bismuth(III) chloride; In toluene; at -40 - 20 ℃; diastereoselective reaction; Inert atmosphere;
DOI:10.1039/c3cc42292e

Reference yield:

: 1073478-35-9
1-C-(6'-O-acetyl-3',4'-di-O-benzyl-2'-O-tosyl-α-D-mannopyranosyl)-acetone

: 1448160-28-8
(2S,3aR,4R,5S,6R,7aR)-2-allyl-4,5-bis(benzyloxy)-6-[(methanesulfonyloxy)methyl]2-methylhexahydro-furo[2,3-b]pyran

Guidance literature:: Multi-step reaction with 3 steps

1.1: diethylamine / methanol / 20 °C

1.2: 8 h / 0 - 20 °C

2.1: potassium carbonate / dimethyl sulfoxide / 5 h / 50 °C

3.1: bismuth(III) chloride / toluene / -40 - 20 °C / Inert atmosphere

With bismuth(III) chloride; potassium carbonate; diethylamine; In methanol; dimethyl sulfoxide; toluene;
DOI:10.1039/c3cc42292e

Reference yield:

: 1448160-10-8
1-C-(3',4'-di-O-benzyl-6'-O-methylsulfonyl-2'-O-tosyl-α-D-mannopyranosyl)-acetone

: 1448160-28-8
(2S,3aR,4R,5S,6R,7aR)-2-allyl-4,5-bis(benzyloxy)-6-[(methanesulfonyloxy)methyl]2-methylhexahydro-furo[2,3-b]pyran

Guidance literature:: Multi-step reaction with 2 steps

1: potassium carbonate / dimethyl sulfoxide / 5 h / 50 °C

2: bismuth(III) chloride / toluene / -40 - 20 °C / Inert atmosphere

With bismuth(III) chloride; potassium carbonate; In dimethyl sulfoxide; toluene;
DOI:10.1039/c3cc42292e