Toluene-4-sulfonic acid (2R,3S,4aR,6R,8S,8aS)-8-benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2R,3S,4aR,6R,8S,8aS)-8-benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester
• CAS No.: 630102-84-0
• Molecular Formula: C₃₄H₄₂O₈S
• Molecular Weight: 610.769

Synonyms:Toluene-4-sulfonic acid (2R,3S,4aR,6R,8S,8aS)-8-benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

Chemical Property of Toluene-4-sulfonic acid (2R,3S,4aR,6R,8S,8aS)-8-benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

Chemical Property:

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Technology Process of Toluene-4-sulfonic acid (2R,3S,4aR,6R,8S,8aS)-8-benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

There total 10 articles about Toluene-4-sulfonic acid (2R,3S,4aR,6R,8S,8aS)-8-benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl 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: 89.0%

p-toluenesulfonyl chloride (98-59-9) + (2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-hydroxymethyl-8a-methyl-octahydro-pyrano[3,2-b]pyran-3-ol (629645-78-9) → Toluene-4-sulfonic acid (2R,3S,4aR,6R,8S,8aS)-8-benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester (630102-84-0)

Guidance literature:

With triethylamine; In dichloromethane; Heating;

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) → Toluene-4-sulfonic acid (2R,3S,4aR,6R,8S,8aS)-8-benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester (630102-84-0)

Guidance literature:

Multi-step reaction with 11 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

With pyridine; dmap; 9-borabicyclo[3.3.1]nonane dimer; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium methylate; potassium hydride; ammonium chloride; ozone; triethylamine; zinc; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 2.1: Barbier allylation;

DOI:10.1016/j.tetlet.2003.09.003

Reference yield:

benzyl bromide (100-39-0) → Toluene-4-sulfonic acid (2R,3S,4aR,6R,8S,8aS)-8-benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester (630102-84-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 100 percent / KH / tetrahydrofuran / 20 °C

2.1: 9-BBN / tetrahydrofuran / 20 °C

2.2: 96 percent / aq. NaOH; H₂O₂ / tetrahydrofuran / 0 °C

3.1: KH / tetrahydrofuran / 20 °C

4.1: CSA / methanol / 20 °C

5.1: 89 percent / Et₃N / CH₂Cl₂ / Heating

With 9-borabicyclo[3.3.1]nonane dimer; camphor-10-sulfonic acid; potassium hydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/j.tetlet.2003.09.003

upstream raw materials:

p-toluenesulfonyl chloride

(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-hydroxymethyl-8a-methyl-octahydro-pyrano[3,2-b]pyran-3-ol

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

benzyl bromide

Downstream raw materials:

[(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acetonitrile

[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

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

[(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

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