Acetic acid (2R,3R,4R,6R)-6-allyl-3-benzyloxy-4-methoxy-5,5-dimethyl-tetrahydro-pyran-2-ylmethyl ester

Base Information

Chemical Name:Acetic acid (2R,3R,4R,6R)-6-allyl-3-benzyloxy-4-methoxy-5,5-dimethyl-tetrahydro-pyran-2-ylmethyl ester
CAS No.:137918-63-9
Molecular Formula:C₂₁H₃₀O₅
Molecular Weight:362.466
Hs Code.:

Synonyms:Acetic acid (2R,3R,4R,6R)-6-allyl-3-benzyloxy-4-methoxy-5,5-dimethyl-tetrahydro-pyran-2-ylmethyl ester

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Chemical Property of Acetic acid (2R,3R,4R,6R)-6-allyl-3-benzyloxy-4-methoxy-5,5-dimethyl-tetrahydro-pyran-2-ylmethyl ester

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Technology Process of Acetic acid (2R,3R,4R,6R)-6-allyl-3-benzyloxy-4-methoxy-5,5-dimethyl-tetrahydro-pyran-2-ylmethyl ester

There total 5 articles about Acetic acid (2R,3R,4R,6R)-6-allyl-3-benzyloxy-4-methoxy-5,5-dimethyl-tetrahydro-pyran-2-ylmethyl ester 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: 93.0%

: 137918-62-8
Acetic acid (2R,4R,5R,6R)-6-acetoxymethyl-5-benzyloxy-4-methoxy-3,3-dimethyl-tetrahydro-pyran-2-yl ester

: 762-72-1
allyl-trimethyl-silane

: 137918-63-9
Acetic acid (2R,3R,4R,6R)-6-allyl-3-benzyloxy-4-methoxy-5,5-dimethyl-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; In acetonitrile; at 0 ℃;
DOI:10.1021/ja00025a056

Reference yield:

: 100-39-0
benzyl bromide

: 137918-63-9
Acetic acid (2R,3R,4R,6R)-6-allyl-3-benzyloxy-4-methoxy-5,5-dimethyl-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 2 steps

2: 93 percent / TMSOTf, BF₃*Et₂O / acetonitrile / 0 °C

With trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; In acetonitrile;
DOI:10.1021/ja00025a056

Reference yield:

: 138050-79-0
(2S,4aR,6S,8aS)-6-Methoxy-7,7-dimethyl-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one

: 137918-63-9
Acetic acid (2R,3R,4R,6R)-6-allyl-3-benzyloxy-4-methoxy-5,5-dimethyl-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: NaBH(OAc)3, CeCl₃ / methanol / 0 °C

2: NaH / tetrahydrofuran / Ambient temperature

With cerium(III) chloride; sodium tris(acetoxy)borohydride; sodium hydride; In tetrahydrofuran; methanol;
DOI:10.1021/ja00025a056