(1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1-phenyl-1-hydroxy-2-propenyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.^9,11.0^2,17.0^8,13]-docosane

Base Information

• Chemical Name: (1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1-phenyl-1-hydroxy-2-propenyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.^9,11.0^2,17.0^8,13]-docosane
• CAS No.: 923986-97-4
• Molecular Formula: C₃₁H₄₄O₃S₂
• Molecular Weight: 528.821

Synonyms:(1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1-phenyl-1-hydroxy-2-propenyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.^9,11.0^2,17.0^8,13]-docosane

Chemical Property of (1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1-phenyl-1-hydroxy-2-propenyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.^9,11.0^2,17.0^8,13]-docosane

Chemical Property:

Purity/Quality:

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Technology Process of (1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1-phenyl-1-hydroxy-2-propenyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.^9,11.0^2,17.0^8,13]-docosane

There total 4 articles about (1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1-phenyl-1-hydroxy-2-propenyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.^9,11.0^2,17.0^8,13]-docosane 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: 98.0%

(1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-benzoyl-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.9,11.02,17.08,13]-docosane (923986-87-2) + vinyl magnesium bromide (1826-67-1) → (1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1-phenyl-1-hydroxy-2-propenyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.9,11.02,17.08,13]-docosane (923986-97-4)

Guidance literature:

In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1021/ol062319f

Reference yield:

2,2-bis[(1S,2R,3S,5R)-2-hydroxymethyl-6,6-dimethylbicyclo[3.1.1]hept-3-ylsulfanyl]-1-phenylethanone (923986-88-3) → (1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1-phenyl-1-hydroxy-2-propenyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.9,11.02,17.08,13]-docosane (923986-97-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / p-TsOH / benzene / 3 h / Heating

2: 98 percent / tetrahydrofuran / -78 - 20 °C

With toluene-4-sulfonic acid; In tetrahydrofuran; benzene;

DOI:10.1021/ol062319f

Reference yield:

(1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1-phenyl-1-hydroxy-ethyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.9,11.02,17.08,13]-docosane (923986-89-4) → (1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1-phenyl-1-hydroxy-2-propenyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.9,11.02,17.08,13]-docosane (923986-97-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NCS; AgNO₃ / acetonitrile; H₂O / 0 - 4 °C

1.2: NaBH₄ / acetonitrile; H₂O / 2 h / 20 °C

2.1: 78 percent / BF₃*Et₂O / CHCl₃ / 3 h / 20 °C

3.1: 91 percent / p-TsOH / benzene / 3 h / Heating

4.1: 98 percent / tetrahydrofuran / -78 - 20 °C

With N-chloro-succinimide; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; silver nitrate; In tetrahydrofuran; chloroform; water; acetonitrile; benzene;

DOI:10.1021/ol062319f

upstream raw materials:

(1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-benzoyl-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.^9,11.0^2,17.0^8,13]-docosane

vinyl magnesium bromide

2,2-bis[(1S,2R,3S,5R)-2-hydroxymethyl-6,6-dimethylbicyclo[3.1.1]hept-3-ylsulfanyl]-1-phenylethanone

(1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1-phenyl-1-hydroxy-ethyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.^9,11.0^2,17.0^8,13]-docosane

Downstream raw materials:

{(1S,2R,3S,5R)-3-mercapto-6,6-dimethylbicyclo[3.1.1]heptan-2-yl}methanol

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