(1S,2R,4R,6S)-4-Benzyloxymethyl-2-methoxy-3,7-dioxa-bicyclo[4.1.0]heptane

Base Information

Chemical Name:(1S,2R,4R,6S)-4-Benzyloxymethyl-2-methoxy-3,7-dioxa-bicyclo[4.1.0]heptane
CAS No.:790667-28-6
Molecular Formula:C₁₄H₁₈O₄
Molecular Weight:250.295
Hs Code.:

Synonyms:(1S,2R,4R,6S)-4-Benzyloxymethyl-2-methoxy-3,7-dioxa-bicyclo[4.1.0]heptane

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Chemical Property of (1S,2R,4R,6S)-4-Benzyloxymethyl-2-methoxy-3,7-dioxa-bicyclo[4.1.0]heptane

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Technology Process of (1S,2R,4R,6S)-4-Benzyloxymethyl-2-methoxy-3,7-dioxa-bicyclo[4.1.0]heptane

There total 8 articles about (1S,2R,4R,6S)-4-Benzyloxymethyl-2-methoxy-3,7-dioxa-bicyclo[4.1.0]heptane 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%

: 790667-31-1
(2R,3R,4S,6R)-6-Benzyloxymethyl-3-bromo-2-methoxy-tetrahydro-pyran-4-ol

: 790667-28-6
(1S,2R,4R,6S)-4-Benzyloxymethyl-2-methoxy-3,7-dioxa-bicyclo[4.1.0]heptane

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 20 ℃; for 4h;
DOI:10.1021/jo0493774

Reference yield:

: 790667-24-2
(2R,6R)-2-[(benzyloxy)methyl]-6-methoxy-3,6-dihydro-2H-pyran

: 790667-28-6
(1S,2R,4R,6S)-4-Benzyloxymethyl-2-methoxy-3,7-dioxa-bicyclo[4.1.0]heptane

: 790667-27-5
(1R,2R,4R,6R)-4-Benzyloxymethyl-2-methoxy-3,7-dioxa-bicyclo[4.1.0]heptane

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 120h;
DOI:10.1021/jo0493774

Reference yield:

: 14618-80-5
(R)-benzyl glycidol

: 790667-28-6
(1S,2R,4R,6S)-4-Benzyloxymethyl-2-methoxy-3,7-dioxa-bicyclo[4.1.0]heptane

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / Ti(O-iPr)4 / tetrahydrofuran / 4 h / -78 - -40 °C

2: pyridine

3: 90 percent / DDQ / CH₂Cl₂; H₂O / 1 h / 20 °C

4: TEA; TMSOTf / methanol / 2 h / 20 °C

5: 74 percent / Raney Ni / tetrahydrofuran / 0.08 h / 20 °C

6: 60.0 mg / m-CPBA / CH₂Cl₂ / 120 h / 20 °C

With pyridine; titanium(IV) isopropylate; trimethylsilyl trifluoromethanesulfonate; TEA; nickel; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1021/jo0493774