(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

Base Information

Chemical Name:(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
CAS No.:256342-03-7
Molecular Formula:C₃₄H₄₆O₁₁
Molecular Weight:630.733
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 20 articles about (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 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%

: 256342-25-3
Benzoic acid (2S,3R,4R,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-yl ester

: 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

Guidance literature:: With methanol; sodium hydroxide; at 25 ℃; for 1h;
DOI:10.1002/(SICI)1521-3773(19991115)38:22<3340::AID-ANIE3340>3.0.CO;2-2

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

: 256342-03-7
(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

Guidance literature:: Multi-step reaction with 7 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

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;
DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8

Reference yield:

: 306726-10-3
(1R,2S,3S)-2,3-Bis-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-1-thiazol-2-yl-butan-1-ol

: 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

Guidance literature:: Multi-step reaction with 8 steps

1.1: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 0 - 25 °C

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

3.1: NaBH₄ / methanol / 0.5 h / 0 °C

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

4.1: 10.97 g / TBAF; AcOH / 2 h / 25 °C

5.1: 85 percent / DBU / CH₂Cl₂ / 0.5 h / 0 °C

6.1: nBu₂SnO / methanol / 3 h / Heating

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

6.3: 10.82 g / PPTS; MeOH / 1 h / 25 °C

7.1: 87 percent / NaH / dimethylformamide / 1 h / 0 - 25 °C

8.1: 95 percent / NaOH; MeOH / diethyl ether / 1 h / 25 °C

With methanol; dmap; 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; triethylamine; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Esterification / 2.1: Methylation / 3.1: Reduction / 3.2: Ring cleavage / 4.1: Cyclization / 5.1: Addition / 6.1: Cyclization / 6.2: Ring cleavage / 6.3: Methanolysis / 7.1: Methylation / 8.1: Debenzoylation;
DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8