[(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid (2R,4aR,6R,7S,8aR,9aS,10aS)-7-allyl-4a,7,10a-trimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-yl ester

Base Information

• Chemical Name: [(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid (2R,4aR,6R,7S,8aR,9aS,10aS)-7-allyl-4a,7,10a-trimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-yl ester
• CAS No.: 629645-84-7
• Molecular Formula: C₅₀H₆₄O₁₁
• Molecular Weight: 841.052

Synonyms:[(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid (2R,4aR,6R,7S,8aR,9aS,10aS)-7-allyl-4a,7,10a-trimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-yl ester

Chemical Property of [(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid (2R,4aR,6R,7S,8aR,9aS,10aS)-7-allyl-4a,7,10a-trimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of [(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid (2R,4aR,6R,7S,8aR,9aS,10aS)-7-allyl-4a,7,10a-trimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-yl ester

There total 21 articles about [(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid (2R,4aR,6R,7S,8aR,9aS,10aS)-7-allyl-4a,7,10a-trimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-yl ester 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: 96.0%

[8-benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid 7-allyl-4a,7,10a-trimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-yl ester (629645-83-6) → [(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid (2R,4aR,6R,7S,8aR,9aS,10aS)-7-allyl-4a,7,10a-trimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-yl ester (629645-84-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.tetlet.2003.09.003

Reference yield:

(2R,4aR,6S,7R,8aS)-6-Methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (131310-61-7) → [(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid (2R,4aR,6R,7S,8aR,9aS,10aS)-7-allyl-4a,7,10a-trimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-yl ester (629645-84-7)

Guidance literature:

Multi-step reaction with 17 steps

1.1: O₃ / methanol / -78 °C

1.2: Me₂S / methanol

2.1: Zn powder; satd. NH₄Cl / tetrahydrofuran / 0 °C

3.1: O₃ / CH₂Cl₂ / -78 °C

3.2: PPh₃ / CH₂Cl₂

4.1: pyridine; DMAP / CH₂Cl₂ / Heating

5.1: 65 percent / BF₃*OEt₂ / acetonitrile / 0 °C

6.1: 98 percent / NaOMe / methanol / 20 °C

7.1: 100 percent / KH / tetrahydrofuran / 20 °C

8.1: 9-BBN / tetrahydrofuran / 20 °C

8.2: 96 percent / aq. NaOH; H₂O₂ / tetrahydrofuran / 0 °C

9.1: KH / tetrahydrofuran / 20 °C

10.1: CSA / methanol / 20 °C

11.1: 89 percent / Et₃N / CH₂Cl₂ / Heating

12.1: 100 percent / DMSO / 50 °C

13.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

14.1: DIBAL-H / CH₂Cl₂ / -78 °C

15.1: aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; tetrahydrofuran / 20 °C

16.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 20 °C

16.2: DMAP / toluene; tetrahydrofuran / 20 °C

17.1: 96 percent / TBAF / tetrahydrofuran / 20 °C

With pyridine; 2,6-dimethylpyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; potassium hydride; diisobutylaluminium hydride; ammonium chloride; ozone; dimethyl sulfoxide; triethylamine; zinc; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; tert-butyl alcohol; 2.1: Barbier allylation / 16.1: Yamaguchi esterification;

DOI:10.1016/j.tetlet.2003.09.003

Reference yield:

(2R,4aR,6R,7S,8aR,9aS,10aS)-4a,7,10a-Trimethyl-2-phenyl-7-vinyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-ol (131311-11-0) → [(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid (2R,4aR,6R,7S,8aR,9aS,10aS)-7-allyl-4a,7,10a-trimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-yl ester (629645-84-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 20 °C

2.1: 9-BBN / tetrahydrofuran / 20 °C

2.2: 89 percent / aq. NaOH; H₂O₂ / tetrahydrofuran / 0 °C

3.1: (COCl)2; DMSO / CH₂Cl₂ / -78 °C

3.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

4.1: NaHMDS / tetrahydrofuran / 0 °C

5.1: 90 percent / TBAF / tetrahydrofuran / 20 °C

6.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 20 °C

6.2: DMAP / toluene; tetrahydrofuran / 20 °C

7.1: 96 percent / TBAF / tetrahydrofuran / 20 °C

With 2,6-dimethylpyridine; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 3.1: Swern oxidation / 4.1: Wittig reaction / 6.1: Yamaguchi esterification;

DOI:10.1016/j.tetlet.2003.09.003

upstream raw materials:

[8-benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid 7-allyl-4a,7,10a-trimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-yl ester

(2R,4aR,6S,7R,8aS)-6-Methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

(2R,4aR,6R,7S,8aR,9aS,10aS)-4a,7,10a-Trimethyl-2-phenyl-7-vinyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-ol

benzyl bromide

Downstream raw materials:

7-allyl-6-[5-benzyloxy-7-(3-benzyloxy-propyl)-10a-methyl-2-vinyl-decahydro-1,8,10-trioxa-anthracen-3-yloxy]-4a,7,10a-trimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracene

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