(2R,3R,4S,5R)-2-(4-Methoxy-benzyloxymethyl)-4,5,6-tris-methoxymethoxy-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (2R,3R,4S,5R)-2-(4-Methoxy-benzyloxymethyl)-4,5,6-tris-methoxymethoxy-tetrahydro-pyran-3-ol
• CAS No.: 583033-32-3
• Molecular Formula: C₂₀H₃₂O₁₀
• Molecular Weight: 432.468

Synonyms:(2R,3R,4S,5R)-2-(4-Methoxy-benzyloxymethyl)-4,5,6-tris-methoxymethoxy-tetrahydro-pyran-3-ol

Chemical Property of (2R,3R,4S,5R)-2-(4-Methoxy-benzyloxymethyl)-4,5,6-tris-methoxymethoxy-tetrahydro-pyran-3-ol

Chemical Property:

Purity/Quality:

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Technology Process of (2R,3R,4S,5R)-2-(4-Methoxy-benzyloxymethyl)-4,5,6-tris-methoxymethoxy-tetrahydro-pyran-3-ol

There total 4 articles about (2R,3R,4S,5R)-2-(4-Methoxy-benzyloxymethyl)-4,5,6-tris-methoxymethoxy-tetrahydro-pyran-3-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: 75.0%

(2R,4aR,7R,8S,8aR)-6,7,8-Tris-methoxymethoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine (583033-22-1) → (2R,3R,4S,5R)-2-(4-Methoxy-benzyloxymethyl)-4,5,6-tris-methoxymethoxy-tetrahydro-pyran-3-ol (583033-32-3) + [(2R,3R,4S,5R)-3-(4-Methoxy-benzyloxy)-4,5,6-tris-methoxymethoxy-tetrahydro-pyran-2-yl]-methanol (583033-24-3)

Guidance literature:

With tetramethylsilane; 3 A molecular sieve; sodium cyanoborohydride; In acetonitrile;

DOI:10.1016/S0960-894X(03)00239-7

Reference yield:

D-Glucose (2280-44-6) → (2R,3R,4S,5R)-2-(4-Methoxy-benzyloxymethyl)-4,5,6-tris-methoxymethoxy-tetrahydro-pyran-3-ol (583033-32-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / TsOH / dimethylformamide / 70 °C / 150 Torr

2: 90 percent / iPr₂NEt / CH₂Cl₂ / 45 °C

3: 75 percent / NaBH₃CN; TFA; 3 A molecular sieves / dimethylformamide

With 3 A molecular sieve; sodium cyanoborohydride; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(03)00239-7

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → (2R,3R,4S,5R)-2-(4-Methoxy-benzyloxymethyl)-4,5,6-tris-methoxymethoxy-tetrahydro-pyran-3-ol (583033-32-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / TsOH / dimethylformamide / 70 °C / 150 Torr

2: 90 percent / iPr₂NEt / CH₂Cl₂ / 45 °C

3: 75 percent / NaBH₃CN; TFA; 3 A molecular sieves / dimethylformamide

With 3 A molecular sieve; sodium cyanoborohydride; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(03)00239-7

upstream raw materials:

(2R,4aR,7R,8S,8aR)-6,7,8-Tris-methoxymethoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine

D-Glucose

p-Anisaldehyde dimethyl acetal

Downstream raw materials:

2-[(2R,3R,4S,5R)-2-(4-Methoxy-benzyloxymethyl)-4,5,6-tris-methoxymethoxy-tetrahydro-pyran-3-yloxymethyl]-quinoline

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