(3R,3aS,6S,6aR)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate

Base Information

• Chemical Name: (3R,3aS,6S,6aR)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate
• CAS No.: 101128-84-1
• Molecular Formula: C₂₀H₂₂O₆S
• Molecular Weight: 390.457

Synonyms:(3R,3aS,6S,6aR)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate

Chemical Property of (3R,3aS,6S,6aR)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate

Chemical Property:

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Technology Process of (3R,3aS,6S,6aR)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate

There total 9 articles about (3R,3aS,6S,6aR)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate 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: 97.0%

(3R,3aS,6S,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate (101222-62-2) + benzyl bromide (100-39-0) → (3R,3aS,6S,6aR)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate (101128-84-1)

Guidance literature:

With potassium hydroxide; tetrabutylammomium bromide; In dichloromethane; water; for 12h; Ambient temperature;

DOI:10.1002/jlac.198519851106

Reference yield: 95.0%

(3R,3aS,6S,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate (101222-62-2) + benzyl chloride (100-44-7) → (3R,3aS,6S,6aR)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate (101128-84-1)

Guidance literature:

With tetrabutylammomium bromide; potassium hydroxide; In dichloromethane; at 20 ℃; for 72h;

DOI:10.1016/j.bmcl.2017.07.027

Reference yield: 94.0%

p-toluenesulfonyl chloride (98-59-9) + (3R,3aR,6S,6aR)-6-(Benzyloxy)hexahydrofuro[3,2-b]furan-3-ol (111956-66-2) → (3R,3aS,6S,6aR)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate (101128-84-1)

Guidance literature:

With pyridine; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1002/ejoc.201600186

upstream raw materials:

(3R,3aS,6S,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate

benzyl bromide

isosorbide 2-acetate

p-toluenesulfonyl chloride

Downstream raw materials:

1,4:3,6-Dianhydro-5-O-benzyl-2-desoxy-L-xylo-hex-1-enit

1,4:3,6-Dianhydro-5-O-benzyl-2-desoxy-L-threo-hex-2-enit

N-benzyl-N-[(3S,3aR,6S,6aS)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-yl]amine

N-benzyl-N-[(3S,3aR,6S,6aS)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-yl]-N-methylamine

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