(2S,3S,4S,5R,6R)-4-Benzyloxy-2-((2S,3R,4R,5S)-4,5-bis-allyloxy-3-benzyloxy-tetrahydro-pyran-2-yloxy)-3-methoxy-5-(4-methoxy-benzyloxy)-6-methoxymethyl-tetrahydro-pyran

Base Information

Chemical Name:(2S,3S,4S,5R,6R)-4-Benzyloxy-2-((2S,3R,4R,5S)-4,5-bis-allyloxy-3-benzyloxy-tetrahydro-pyran-2-yloxy)-3-methoxy-5-(4-methoxy-benzyloxy)-6-methoxymethyl-tetrahydro-pyran
CAS No.:256342-04-8
Molecular Formula:C₄₁H₅₂O₁₁
Molecular Weight:720.857
Hs Code.:

(2S,3S,4S,5R,6R)-4-Benzyloxy-2-((2S,3R,4R,5S)-4,5-bis-allyloxy-3-benzyloxy-tetrahydro-pyran-2-yloxy)-3-methoxy-5-(4-methoxy-benzyloxy)-6-methoxymethyl-tetrahydro-pyran

Synonyms:(2S,3S,4S,5R,6R)-4-Benzyloxy-2-((2S,3R,4R,5S)-4,5-bis-allyloxy-3-benzyloxy-tetrahydro-pyran-2-yloxy)-3-methoxy-5-(4-methoxy-benzyloxy)-6-methoxymethyl-tetrahydro-pyran

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Chemical Property of (2S,3S,4S,5R,6R)-4-Benzyloxy-2-((2S,3R,4R,5S)-4,5-bis-allyloxy-3-benzyloxy-tetrahydro-pyran-2-yloxy)-3-methoxy-5-(4-methoxy-benzyloxy)-6-methoxymethyl-tetrahydro-pyran

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Technology Process of (2S,3S,4S,5R,6R)-4-Benzyloxy-2-((2S,3R,4R,5S)-4,5-bis-allyloxy-3-benzyloxy-tetrahydro-pyran-2-yloxy)-3-methoxy-5-(4-methoxy-benzyloxy)-6-methoxymethyl-tetrahydro-pyran

There total 21 articles about (2S,3S,4S,5R,6R)-4-Benzyloxy-2-((2S,3R,4R,5S)-4,5-bis-allyloxy-3-benzyloxy-tetrahydro-pyran-2-yloxy)-3-methoxy-5-(4-methoxy-benzyloxy)-6-methoxymethyl-tetrahydro-pyran 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: 90.0%

: 100-39-0
benzyl bromide

: 256342-03-7
(2S,3R,4S,5S)-4,5-Bis-allyloxy-2-[(2S,3S,4S,5R,6R)-4-benzyloxy-3-methoxy-5-(4-methoxy-benzyloxy)-6-methoxymethyl-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-3-ol

: 256342-04-8
(2S,3S,4S,5R,6R)-4-Benzyloxy-2-((2S,3R,4R,5S)-4,5-bis-allyloxy-3-benzyloxy-tetrahydro-pyran-2-yloxy)-3-methoxy-5-(4-methoxy-benzyloxy)-6-methoxymethyl-tetrahydro-pyran

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at 0 - 25 ℃; for 4h;
DOI:10.1002/(SICI)1521-3773(19991115)38:22<3340::AID-ANIE3340>3.0.CO;2-2

Reference yield:

: Trifluoro-methanesulfonate2-[(1R,2R,3S)-2,3-bis-allyloxy-1-benzoyloxy-4-(tert-butyl-diphenyl-silanyloxy)-butyl]-3-methyl-thiazol-3-ium;

: 256342-04-8
(2S,3S,4S,5R,6R)-4-Benzyloxy-2-((2S,3R,4R,5S)-4,5-bis-allyloxy-3-benzyloxy-tetrahydro-pyran-2-yloxy)-3-methoxy-5-(4-methoxy-benzyloxy)-6-methoxymethyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaBH₄ / methanol / 0.5 h / 0 °C

1.2: H₂O; CuCl₂; CuO / acetonitrile / 2 h / 25 °C

2.1: 10.97 g / TBAF; AcOH / 2 h / 25 °C

3.1: 85 percent / DBU / CH₂Cl₂ / 0.5 h / 0 °C

4.1: nBu₂SnO / methanol / 3 h / Heating

4.2: TMSOTf / CH₂Cl₂ / 12 h / 0 - 25 °C

4.3: 10.82 g / PPTS; MeOH / 1 h / 25 °C

5.1: 87 percent / NaH / dimethylformamide / 1 h / 0 - 25 °C

6.1: 95 percent / NaOH; MeOH / diethyl ether / 1 h / 25 °C

7.1: NaH / dimethylformamide / 0.08 h / 0 °C

7.2: 90 percent / nBu₄NI / dimethylformamide / 4 h / 0 - 25 °C

With methanol; sodium hydroxide; sodium tetrahydroborate; tetrabutyl ammonium fluoride; sodium hydride; di(n-butyl)tin oxide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1.1: Reduction / 1.2: Ring cleavage / 2.1: Cyclization / 3.1: Addition / 4.1: Cyclization / 4.2: Ring cleavage / 4.3: Methanolysis / 5.1: Methylation / 6.1: Debenzoylation / 7.1: Metallation / 7.2: Etherification;
DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8

Reference yield:

: 306726-12-5
Benzoic acid (1R,2R,3S)-2,3-bis-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-1-thiazol-2-yl-butyl ester

: 256342-04-8
(2S,3S,4S,5R,6R)-4-Benzyloxy-2-((2S,3R,4R,5S)-4,5-bis-allyloxy-3-benzyloxy-tetrahydro-pyran-2-yloxy)-3-methoxy-5-(4-methoxy-benzyloxy)-6-methoxymethyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 8 steps

1.1: molecular sieves 4 Angstroem / acetonitrile / 0.25 h / 25 °C

2.1: NaBH₄ / methanol / 0.5 h / 0 °C

2.2: H₂O; CuCl₂; CuO / acetonitrile / 2 h / 25 °C

3.1: 10.97 g / TBAF; AcOH / 2 h / 25 °C

4.1: 85 percent / DBU / CH₂Cl₂ / 0.5 h / 0 °C

5.1: nBu₂SnO / methanol / 3 h / Heating

5.2: TMSOTf / CH₂Cl₂ / 12 h / 0 - 25 °C

5.3: 10.82 g / PPTS; MeOH / 1 h / 25 °C

6.1: 87 percent / NaH / dimethylformamide / 1 h / 0 - 25 °C

7.1: 95 percent / NaOH; MeOH / diethyl ether / 1 h / 25 °C

8.1: NaH / dimethylformamide / 0.08 h / 0 °C

8.2: 90 percent / nBu₄NI / dimethylformamide / 4 h / 0 - 25 °C

With methanol; sodium hydroxide; sodium tetrahydroborate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium hydride; di(n-butyl)tin oxide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Methylation / 2.1: Reduction / 2.2: Ring cleavage / 3.1: Cyclization / 4.1: Addition / 5.1: Cyclization / 5.2: Ring cleavage / 5.3: Methanolysis / 6.1: Methylation / 7.1: Debenzoylation / 8.1: Metallation / 8.2: Etherification;
DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8