tert-Butyl-dimethyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-silane

Base Information

• Chemical Name: tert-Butyl-dimethyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-silane
• CAS No.: 123487-60-5
• Molecular Formula: C₃₈H₅₂O₆Si
• Molecular Weight: 632.913

Synonyms:tert-Butyl-dimethyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-silane

Chemical Property of tert-Butyl-dimethyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-silane

Chemical Property:

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Technology Process of tert-Butyl-dimethyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-silane

There total 3 articles about tert-Butyl-dimethyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-silane 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:

((3aS,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-5-ylmethoxy)-tert-butyl-dimethyl-silane → tert-Butyl-dimethyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-silane (123487-60-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / Yb(OTf)3

2: NaOMe

With sodium methylate; ytterbium(III) triflate;

DOI:10.1016/j.bmcl.2004.04.103

Reference yield:

Benzoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-pent-4-enyloxy-tetrahydro-pyran-3-yl ester (737788-39-5) → tert-Butyl-dimethyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-silane (123487-60-5)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe

With sodium methylate;

DOI:10.1016/j.bmcl.2004.04.103

Reference yield:

benzyl bromide (100-39-0) + (2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-pent-4-enyloxy-tetrahydro-pyran-3-ol → tert-Butyl-dimethyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-silane (123487-60-5)

Guidance literature:

DOI:10.1016/j.bmcl.2004.04.103

upstream raw materials:

benzyl bromide

Benzoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-pent-4-enyloxy-tetrahydro-pyran-3-yl ester

Downstream raw materials:

tert-Butyl-dimethyl-[(2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-tetrahydro-pyran-2-ylmethoxy]-silane

tert-Butyl-dimethyl-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-tetrahydro-pyran-2-ylmethoxy]-silane

tert-Butyl-dimethyl-{(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-tetrahydro-pyran-2-ylmethoxy}-silane

tert-Butyl-dimethyl-{(2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-tetrahydro-pyran-2-ylmethoxy}-silane

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