[(2S,3S,4aR,5R,7R,8R,8aS)-8-Benzyloxy-7-((3aR,5R,6R,6aR)-5-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy)-2,3-dimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-5-yl]-methanol

Base Information

Chemical Name:[(2S,3S,4aR,5R,7R,8R,8aS)-8-Benzyloxy-7-((3aR,5R,6R,6aR)-5-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy)-2,3-dimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-5-yl]-methanol
CAS No.:300693-14-5
Molecular Formula:C₂₇H₄₀O₁₂
Molecular Weight:556.607
Hs Code.:

[(2S,3S,4aR,5R,7R,8R,8aS)-8-Benzyloxy-7-((3aR,5R,6R,6aR)-5-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy)-2,3-dimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-5-yl]-methanol

Synonyms:[(2S,3S,4aR,5R,7R,8R,8aS)-8-Benzyloxy-7-((3aR,5R,6R,6aR)-5-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy)-2,3-dimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-5-yl]-methanol

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Chemical Property of [(2S,3S,4aR,5R,7R,8R,8aS)-8-Benzyloxy-7-((3aR,5R,6R,6aR)-5-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy)-2,3-dimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-5-yl]-methanol

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Technology Process of [(2S,3S,4aR,5R,7R,8R,8aS)-8-Benzyloxy-7-((3aR,5R,6R,6aR)-5-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy)-2,3-dimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-5-yl]-methanol

There total 5 articles about [(2S,3S,4aR,5R,7R,8R,8aS)-8-Benzyloxy-7-((3aR,5R,6R,6aR)-5-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy)-2,3-dimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-5-yl]-methanol 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: 95.0%

: 300693-13-4
(2''S,3''S) 3-O-(2'-O-benzyl-6-O-t-butyldiphenylsilyl-3',4'-di-O-(2'',3''-dimethoxybutane-2'',3''-diyl)-α-D-glucopyranosyl)-1,2-O-isopropylidene-5-O-t-butyldiphenylsilyl-α-D-ribofuranoside

: 300693-14-5
[(2S,3S,4aR,5R,7R,8R,8aS)-8-Benzyloxy-7-((3aR,5R,6R,6aR)-5-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy)-2,3-dimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-5-yl]-methanol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; 1,4-dioxane; at 50 ℃; for 16h;
DOI:10.1016/S0040-4020(00)00480-4

Reference yield:

: 100-39-0
benzyl bromide

: 300693-14-5
[(2S,3S,4aR,5R,7R,8R,8aS)-8-Benzyloxy-7-((3aR,5R,6R,6aR)-5-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy)-2,3-dimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-5-yl]-methanol

Guidance literature:: Multi-step reaction with 3 steps

1: 4.40 g / NaH / dimethylformamide / 0 °C

2: 74 percent / TfOH / toluene; dioxane / 0.25 h

3: 95 percent / TBAF / tetrahydrofuran; dioxane / 16 h / 50 °C

With trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; toluene; 1: Substitution / 2: Substitution / 3: Hydrolysis;
DOI:10.1016/S0040-4020(00)00480-4

Reference yield:

: 197644-79-4
(2'S,3'S)-ethyl 3,4-di-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-β-D-glucopyranoside

: 300693-14-5
[(2S,3S,4aR,5R,7R,8R,8aS)-8-Benzyloxy-7-((3aR,5R,6R,6aR)-5-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy)-2,3-dimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-5-yl]-methanol

Guidance literature:: Multi-step reaction with 4 steps

1: pyridine / 2 h

2: 4.40 g / NaH / dimethylformamide / 0 °C

3: 74 percent / TfOH / toluene; dioxane / 0.25 h

4: 95 percent / TBAF / tetrahydrofuran; dioxane / 16 h / 50 °C

With pyridine; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; toluene; 1: Substitution / 2: Substitution / 3: Substitution / 4: Hydrolysis;
DOI:10.1016/S0040-4020(00)00480-4