(2S,6S)-2-[(benzyloxy)methyl]-6-methoxy-3,6-dihydro-2H-pyran

Base Information

• Chemical Name: (2S,6S)-2-[(benzyloxy)methyl]-6-methoxy-3,6-dihydro-2H-pyran
• CAS No.: 130857-02-2
• Molecular Formula: C₁₄H₁₈O₃
• Molecular Weight: 234.295
• Mol file: 130857-02-2.mol

Synonyms:(2S,6S)-2-[(benzyloxy)methyl]-6-methoxy-3,6-dihydro-2H-pyran

Chemical Property of (2S,6S)-2-[(benzyloxy)methyl]-6-methoxy-3,6-dihydro-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of (2S,6S)-2-[(benzyloxy)methyl]-6-methoxy-3,6-dihydro-2H-pyran

There total 12 articles about (2S,6S)-2-[(benzyloxy)methyl]-6-methoxy-3,6-dihydro-2H-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:

6(S)-carboxymethyl-2-methoxy-5,6-dihydro-2H-pyran (646058-48-2) → (2S,6S)-2-[(benzyloxy)methyl]-6-methoxy-3,6-dihydro-2H-pyran (130857-02-2)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAlH₄ / diethyl ether / 1 h / Ambient temperature

2: 1.) NaH / 1.) THF, reflux, 2 h, 2.) THF, reflux, 30 min

With lithium aluminium tetrahydride; sodium hydride; In diethyl ether;

DOI:10.1021/ja00086a014

Reference yield:

(5S,7S)-7-[(benzyloxy)methyl]-5-methoxy-2,3,7,8-tetrahydro-5H-[1,4]dithiino[2,3-c]pyran (790667-32-2) → (2S,6S)-2-[(benzyloxy)methyl]-6-methoxy-3,6-dihydro-2H-pyran (130857-02-2)

Guidance literature:

With nickel; In tetrahydrofuran; at 20 ℃; for 0.0833333h;

DOI:10.1021/jo0493774

Reference yield:

(S)-benzyl glycidyl ether (2930-05-4,14618-80-5,89616-40-0,16495-13-9) → (2S,6S)-2-[(benzyloxy)methyl]-6-methoxy-3,6-dihydro-2H-pyran (130857-02-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 89 percent / Ti(O-iPr)4 / tetrahydrofuran / 4 h / -78 - -40 °C

2: pyridine

3: DDQ / CH₂Cl₂; H₂O / 1 h / 20 °C

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

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

With pyridine; titanium(IV) isopropylate; trimethylsilyl trifluoromethanesulfonate; TEA; nickel; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/jo0493774

upstream raw materials:

(2S,6S)-6-hydroxymethyl-2-methoxy-5,6-dihydro-2H-pyran

benzyl bromide

5,6-dihydro-6-(hydroxymethyl)-2-methoxy-2H-pyran

(5S,7S)-7-[(benzyloxy)methyl]-5-methoxy-2,3,7,8-tetrahydro-5H-[1,4]dithiino[2,3-c]pyran

Downstream raw materials:

(6S)-6-[(phenylmethoxy)methyl]-5,6-dihydro-2H-pyran-2-one

methyl 6-O-benzyl-4-deoxy-α-D-lyxo-hexopyranoside