(3aS,4R,6R,6aS)-4-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde

Base Information

Chemical Name:(3aS,4R,6R,6aS)-4-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde
CAS No.:175910-03-9
Molecular Formula:C₄₁H₅₀O₁₂
Molecular Weight:734.841
Hs Code.:

(3aS,4R,6R,6aS)-4-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde

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Chemical Property of (3aS,4R,6R,6aS)-4-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde

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Technology Process of (3aS,4R,6R,6aS)-4-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde

There total 3 articles about (3aS,4R,6R,6aS)-4-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde 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:

: 19488-48-3
methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

: 175910-03-9
(3aS,4R,6R,6aS)-4-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde

Guidance literature:: Multi-step reaction with 2 steps

1: 62 percent / trimethylsilyl triflate, activated 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / Ambient temperature

2: 1.) MeOTf, activated 4 Angstroem molecular sieves, 2.) NaBH₄, 3.) CuO, CuCl₂*2H₂O

With sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; methyl trifluoromethanesulfonate; copper(II) oxide; In dichloromethane;
DOI:10.1016/0040-4020(95)01095-5

Reference yield:

: 160584-08-7
1-O-Acetyl-2,3:5,6-di-O-isopropylidene-1-(2-thiazolyl)-α-D-mannofuranose

: 175910-03-9
(3aS,4R,6R,6aS)-4-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde

Guidance literature:: Multi-step reaction with 2 steps

1: 62 percent / trimethylsilyl triflate, activated 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / Ambient temperature

2: 1.) MeOTf, activated 4 Angstroem molecular sieves, 2.) NaBH₄, 3.) CuO, CuCl₂*2H₂O

With sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; methyl trifluoromethanesulfonate; copper(II) oxide; In dichloromethane;
DOI:10.1016/0040-4020(95)01095-5

Reference yield:

: 175909-99-6
methyl 2,3,6-tri-O-benzyl-4-O-[2,3:5,6-di-O-isopropylidene-1-C-(2-thiazolyl)-α-D-mannofuranosyl]-α-D-glucopyranoside

: 175910-03-9
(3aS,4R,6R,6aS)-4-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde

Guidance literature:: With sodium tetrahydroborate; 4 A molecular sieve; methyl trifluoromethanesulfonate; copper(II) oxide; Yield given. Multistep reaction;
DOI:10.1016/0040-4020(95)01095-5