(2S,3R,4S,6R)-3-Benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-ol

Base Information

• Chemical Name: (2S,3R,4S,6R)-3-Benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-ol
• CAS No.: 451505-76-3
• Molecular Formula: C₁₄H₂₀O₄
• Molecular Weight: 252.31
• Mol file: 451505-76-3.mol

Synonyms:(2S,3R,4S,6R)-3-Benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-ol

Chemical Property of (2S,3R,4S,6R)-3-Benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,6R)-3-Benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-ol

There total 17 articles about (2S,3R,4S,6R)-3-Benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-ol 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: 99.0%

Acetic acid (2S,3R,4S,6R)-3-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yl ester (294178-41-9) → (2S,3R,4S,6R)-3-Benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-ol (451505-76-3)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1016/S0960-894X(02)00209-3

Reference yield: 32.0%

(2S,3R,4S,6R)-3-Benzyloxy-2-methoxy-4-methoxymethoxy-6-methyl-tetrahydro-pyran (454479-46-0) → (2S,3R,4S,6R)-3-Benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-ol (451505-76-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane;

DOI:10.1016/S0960-894X(02)00209-3

Reference yield:

(2S,3R,4R,5S,6R)-5-chloro-6-(chloromethyl)-2-methoxytetrahydro-2H-pyran-3,4-diol (4990-91-4) → (2S,3R,4S,6R)-3-Benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-ol (451505-76-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 80 percent / n-Bu₃SnH; AIBN / toluene

2.1: (n-Bu₃Sn)2O / toluene

2.3: Et₃N / CH₂Cl₂

3.1: 99 percent / NaOMe / methanol

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium methylate; bis(tri-n-butyltin)oxide; In methanol; toluene;

DOI:10.1016/S0960-894X(02)00209-3

upstream raw materials:

Acetic acid (2S,3R,4S,6R)-3-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yl ester

methyl 4,6-dideoxy-α-D-glucopyranoside

benzyl bromide

(2S,3R,4S,6R)-3-Benzyloxy-2-methoxy-4-methoxymethoxy-6-methyl-tetrahydro-pyran

Downstream raw materials:

Phosphoric acid (2R,3R,4S,6R)-4-azido-3-benzyloxy-6-methyl-tetrahydro-pyran-2-yl ester dibenzyl ester

(2S,3R,4S,6R)-4-Azido-3-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran

(2S,3R,4R,6R)-3-Benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-ol