(3'S,4'R)-3'-(p-methoxybenzyloxy)tetrahydrofuran-4'-yl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside

Base Information

Chemical Name:(3'S,4'R)-3'-(p-methoxybenzyloxy)tetrahydrofuran-4'-yl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside
CAS No.:473441-54-2
Molecular Formula:C₃₆H₄₂O₁₁
Molecular Weight:650.723
Hs Code.:

Synonyms:(3'S,4'R)-3'-(p-methoxybenzyloxy)tetrahydrofuran-4'-yl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside

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Chemical Property of (3'S,4'R)-3'-(p-methoxybenzyloxy)tetrahydrofuran-4'-yl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside

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Technology Process of (3'S,4'R)-3'-(p-methoxybenzyloxy)tetrahydrofuran-4'-yl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside

There total 4 articles about (3'S,4'R)-3'-(p-methoxybenzyloxy)tetrahydrofuran-4'-yl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside 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: 63.0%

: 221356-67-8
(3R,4S)-4-(p-methoxybenzyloxy)-tetrahydrofuran-3-ol

: 264230-04-8
3,4-di-O-acetyl-2,6-di-O-benzyl-D-glucopyranosyl dimethyl phosphite

: 473441-54-2
(3'S,4'R)-3'-(p-methoxybenzyloxy)tetrahydrofuran-4'-yl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside

Guidance literature:: With 4 A molecular sieve; silver perchlorate; zinc(II) chloride; In 1,4-dioxane; toluene; for 18h;
DOI:10.1016/S0008-6215(02)00103-9

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 473441-54-2
(3'S,4'R)-3'-(p-methoxybenzyloxy)tetrahydrofuran-4'-yl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: PTSA / dimethylformamide / 3 h / 70 °C

1.2: 90 percent / DIBAL-H / CH₂Cl₂ / 4 h / -78 °C

2.1: pyridine / 65 h / 0 - 20 °C

3.1: 94 percent / NaOH / methanol / 1 h / Heating

4.1: 63 percent / 4 Angstroem mol. sieves; ZnCl₂; AgClO₄ / toluene; dioxane / 18 h

With pyridine; sodium hydroxide; 4 A molecular sieve; silver perchlorate; toluene-4-sulfonic acid; zinc(II) chloride; In 1,4-dioxane; methanol; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0008-6215(02)00103-9

Reference yield:

: cis-4-(p-methoxybenzyloxy)-tetrahydrofuran-3-ol

: 473441-54-2
(3'S,4'R)-3'-(p-methoxybenzyloxy)tetrahydrofuran-4'-yl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: pyridine / 65 h / 0 - 20 °C

2: 94 percent / NaOH / methanol / 1 h / Heating

3: 63 percent / 4 Angstroem mol. sieves; ZnCl₂; AgClO₄ / toluene; dioxane / 18 h

With pyridine; sodium hydroxide; 4 A molecular sieve; silver perchlorate; zinc(II) chloride; In 1,4-dioxane; methanol; toluene;
DOI:10.1016/S0008-6215(02)00103-9