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

Base Information

Chemical Name:(2R,3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-methyl-2-(2-methylallyl)hexahydro-furo[2,3-b]pyran
CAS No.:1448160-17-5
Molecular Formula:C₃₄H₄₀O₅
Molecular Weight:528.689
Hs Code.:

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

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

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

There total 3 articles about (2R,3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-methyl-2-(2-methylallyl)hexahydro-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: 81.0%

: 18292-38-1
2-methallyltrimethylsilane

: acetyl-2-C-acetonyl-2-deoxy-3,4,6-tri-O-benzyl-D-glucopyranoside

: 1448160-17-5
(2R,3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-methyl-2-(2-methylallyl)hexahydro-furo[2,3-b]pyran

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at -40 - 20 ℃; for 2h; diastereoselective reaction; Molecular sieve; Inert atmosphere;
DOI:10.1039/c4ob00642a

Reference yield: 75.0%

: 18292-38-1
2-methallyltrimethylsilane

: 857419-75-1
1-C-acetyl-3,4,6-tri-O-benzyl-1,2-cyclopropane-1,2-deoxy-α-D-glucopyranose

: 1448160-17-5
(2R,3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-methyl-2-(2-methylallyl)hexahydro-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:

: methyl 3,4,6-tri-O-benzyl-2-C-acetylmethyl-2-deoxy-β-D-glucopyranoside

: 1448160-17-5
(2R,3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-methyl-2-(2-methylallyl)hexahydro-furo[2,3-b]pyran

Guidance literature:: Multi-step reaction with 2 steps

1: acetic acid; sulfuric acid / 0.5 h / 0 °C

2: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 2 h / -40 - 20 °C / Molecular sieve; Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; sulfuric acid; acetic acid; In acetonitrile;
DOI:10.1039/c4ob00642a