(+)-(19S,20S)-19,20-bis((phenylmethoxy)methyl)-27,28,29,30-tetrakis(phenylmethoxy)-18,21-dioxapentacyclo<21.3.1.1^2,6.1^7,11.1^12,16>triaconta-1(27),2,4,6(30),7,9,11(29),12,14,16(28),23,25-dodecaene

Base Information

• Chemical Name: (+)-(19S,20S)-19,20-bis((phenylmethoxy)methyl)-27,28,29,30-tetrakis(phenylmethoxy)-18,21-dioxapentacyclo<21.3.1.1^2,6.1^7,11.1^12,16>triaconta-1(27),2,4,6(30),7,9,11(29),12,14,16(28),23,25-dodecaene
• CAS No.: 123292-09-1
• Molecular Formula: C₇₂H₆₄O₈
• Molecular Weight: 1057.3

Synonyms:(+)-(19S,20S)-19,20-bis((phenylmethoxy)methyl)-27,28,29,30-tetrakis(phenylmethoxy)-18,21-dioxapentacyclo<21.3.1.1^2,6.1^7,11.1^12,16>triaconta-1(27),2,4,6(30),7,9,11(29),12,14,16(28),23,25-dodecaene

Chemical Property of (+)-(19S,20S)-19,20-bis((phenylmethoxy)methyl)-27,28,29,30-tetrakis(phenylmethoxy)-18,21-dioxapentacyclo<21.3.1.1^2,6.1^7,11.1^12,16>triaconta-1(27),2,4,6(30),7,9,11(29),12,14,16(28),23,25-dodecaene

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Technology Process of (+)-(19S,20S)-19,20-bis((phenylmethoxy)methyl)-27,28,29,30-tetrakis(phenylmethoxy)-18,21-dioxapentacyclo<21.3.1.1^2,6.1^7,11.1^12,16>triaconta-1(27),2,4,6(30),7,9,11(29),12,14,16(28),23,25-dodecaene

There total 6 articles about (+)-(19S,20S)-19,20-bis((phenylmethoxy)methyl)-27,28,29,30-tetrakis(phenylmethoxy)-18,21-dioxapentacyclo<21.3.1.1^2,6.1^7,11.1^12,16>triaconta-1(27),2,4,6(30),7,9,11(29),12,14,16(28),23,25-dodecaene 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: 15.0%

(2S,3S)-1,4-bis(benzyloxy)-2,3-butanediol (17401-06-8) + 3,3'''-bis(bromomethyl)-2,2',2'',2'''-tetrakis(phenylmethoxy)-<1,1':3',1'':3'',1'''>-quaterphenyl (123291-88-3) → (+)-(19S,20S)-19,20-bis((phenylmethoxy)methyl)-27,28,29,30-tetrakis(phenylmethoxy)-18,21-dioxapentacyclo<21.3.1.12,6.17,11.112,16>triaconta-1(27),2,4,6(30),7,9,11(29),12,14,16(28),23,25-dodecaene (123292-09-1)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 42h; Heating;

DOI:10.1021/jo00284a018

Reference yield:

benzyl bromide (100-39-0) → (+)-(19S,20S)-19,20-bis((phenylmethoxy)methyl)-27,28,29,30-tetrakis(phenylmethoxy)-18,21-dioxapentacyclo<21.3.1.12,6.17,11.112,16>triaconta-1(27),2,4,6(30),7,9,11(29),12,14,16(28),23,25-dodecaene (123292-09-1)

Guidance literature:

Multi-step reaction with 6 steps

1: K₂CO₃ / acetone / 168 h / Heating

2: NaOH / ethanol; H₂O / 8 h / Heating

3: 100 percent / K₂CO₃ / acetone / 15 h / Heating

4: 87 percent / LiAlH₄ / diethyl ether / 0.67 h / 0 °C

5: 70 percent / PBr₃ / benzene / 3 h / 25 °C

6: 15 percent / NaH / tetrahydrofuran / 42 h / Heating

With sodium hydroxide; lithium aluminium tetrahydride; phosphorus tribromide; sodium hydride; potassium carbonate; In tetrahydrofuran; diethyl ether; ethanol; water; acetone; benzene;

DOI:10.1021/jo00284a018

Reference yield:

2,2',2'',2'''-tetrakis(phenylmethoxy)-<1,1':3'',1'':1'''-quaterphenyl>-3,3'''-dimethanol (123291-87-2) → (+)-(19S,20S)-19,20-bis((phenylmethoxy)methyl)-27,28,29,30-tetrakis(phenylmethoxy)-18,21-dioxapentacyclo<21.3.1.12,6.17,11.112,16>triaconta-1(27),2,4,6(30),7,9,11(29),12,14,16(28),23,25-dodecaene (123292-09-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / PBr₃ / benzene / 3 h / 25 °C

2: 15 percent / NaH / tetrahydrofuran / 42 h / Heating

With phosphorus tribromide; sodium hydride; In tetrahydrofuran; benzene;

DOI:10.1021/jo00284a018

upstream raw materials:

(2S,3S)-1,4-bis(benzyloxy)-2,3-butanediol

3,3'''-bis(bromomethyl)-2,2',2'',2'''-tetrakis(phenylmethoxy)-<1,1':3',1'':3'',1'''>-quaterphenyl

benzyl bromide

2,2',2'',2'''-tetrakis(phenylmethoxy)-<1,1':3'',1'':1'''-quaterphenyl>-3,3'''-dimethanol

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