(3aS,4R,6S,6aR)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-[(E)-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-vinyl]-tetrahydro-furo[3,4-d][1,3]dioxole

Base Information

Chemical Name:(3aS,4R,6S,6aR)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-[(E)-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-vinyl]-tetrahydro-furo[3,4-d][1,3]dioxole
CAS No.:565204-95-7
Molecular Formula:C₄₁H₅₀O₁₀
Molecular Weight:702.842
Hs Code.:

(3aS,4R,6S,6aR)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-[(E)-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-vinyl]-tetrahydro-furo[3,4-d][1,3]dioxole

Synonyms:(3aS,4R,6S,6aR)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-[(E)-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-vinyl]-tetrahydro-furo[3,4-d][1,3]dioxole

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Chemical Property of (3aS,4R,6S,6aR)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-[(E)-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-vinyl]-tetrahydro-furo[3,4-d][1,3]dioxole

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Technology Process of (3aS,4R,6S,6aR)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-[(E)-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-vinyl]-tetrahydro-furo[3,4-d][1,3]dioxole

There total 5 articles about (3aS,4R,6S,6aR)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-[(E)-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-vinyl]-tetrahydro-furo[3,4-d][1,3]dioxole 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: 50.0%

: (3aS,4R,6aS)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethanesulfonylmethyl)-tetrahydro-furo[3,4-d][1,3]dioxole

: 565204-95-7
(3aS,4R,6S,6aR)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-[(E)-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-vinyl]-tetrahydro-furo[3,4-d][1,3]dioxole

Guidance literature:: With aluminum oxide; potassium hydroxide; dibromodifluoromethane; In dichloromethane; tert-butyl alcohol; at 5 ℃; for 2h;
DOI:10.1002/anie.200390356

Reference yield:

: 7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4
2,3,5,6-di-O-isopropylidene-D-mannofuranose

: 565204-95-7
(3aS,4R,6S,6aR)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-[(E)-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-vinyl]-tetrahydro-furo[3,4-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 2 steps

1: 86 percent / sodium hydride / tetrahydrofuran / -78 °C

2: 50 percent / KOH/Al₂O₃; CBr₂F₂ / CH₂Cl₂; 2-methyl-propan-2-ol / 2 h / 5 °C

With aluminum oxide; potassium hydroxide; dibromodifluoromethane; sodium hydride; In tetrahydrofuran; dichloromethane; tert-butyl alcohol; 1: Horner-Wadsworth-Emmons reaction / 2: Ramberg-Baecklund reaction;
DOI:10.1002/anie.200390356

Reference yield:

: 252851-40-4
methyl 2,3,4-tri-O-benzyl-6-deoxy-6-mercapto-α-D-glucopyranoside

: 565204-95-7
(3aS,4R,6S,6aR)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-[(E)-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-vinyl]-tetrahydro-furo[3,4-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 4 steps

1: K₂CO₃ / acetone

2: oxone / tetrahydrofuran; aq. methanol

3: 86 percent / sodium hydride / tetrahydrofuran / -78 °C

4: 50 percent / KOH/Al₂O₃; CBr₂F₂ / CH₂Cl₂; 2-methyl-propan-2-ol / 2 h / 5 °C

With aluminum oxide; Oxone; potassium hydroxide; dibromodifluoromethane; sodium hydride; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; acetone; tert-butyl alcohol; 3: Horner-Wadsworth-Emmons reaction / 4: Ramberg-Baecklund reaction;
DOI:10.1002/anie.200390356